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87120-72-7

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87120-72-7 Usage

Description

4-Amino-1-Boc-piperidine, also known as tert-butyl 4-aminopiperidine-1-carboxylate, is a chemical compound that serves as an important building block in the synthesis of various pharmaceutical compounds. It is characterized by the presence of a piperidine ring with an amino group at the 4-position and a Boc-protecting group at the 1-position. This structure allows for versatile synthetic applications in medicinal chemistry.

Uses

Used in Pharmaceutical Synthesis:
4-Amino-1-Boc-piperidine is used as a chemical reagent for the preparation of pharmaceutical compounds. Its unique structure allows for the synthesis of a wide range of biologically active molecules, making it a valuable intermediate in the development of new drugs.
Used in Bromodomain Inhibitors Synthesis:
In the field of anti-tumor therapy, 4-Amino-1-Boc-piperidine is used as a key component in the synthesis of bromodomain inhibitors. These inhibitors play a crucial role in regulating gene expression and cell cycle progression, making them potential therapeutic agents for the treatment of various cancers.
Used in HepG2 Cell Cycle Inhibitors Synthesis:
4-Amino-1-Boc-piperidine is also employed in the synthesis of HepG2 cell cycle inhibitors, which are used in anti-tumor therapy. These inhibitors target specific cell cycle proteins, leading to the arrest of cell division and the prevention of tumor growth.
Used in Microwave-Assisted Solid-Phase Synthesis:
4-Amino-1-Boc-piperidine is utilized in a microwave-assisted solid-phase synthesis of N-substituted piperidines. This method involves the direct annulation of primary amines with resin-bound dimesylates, allowing for the efficient and rapid synthesis of a variety of N-substituted piperidine derivatives.
Used in CCR5 Receptor Inhibition:
4-Amino-1-Boc-piperidine is a potent inhibitor of the CCR5 receptor, which is involved in the growth and proliferation of cancer cells. By targeting the CCR5 receptor, this compound is able to inhibit the growth of cancer cells and has been shown to be effective in blocking the production of cytokines, such as interleukin 2, that are necessary for cell division and growth.
Used in X-Ray Crystal Structure Analysis:
The x-ray crystal structure of 4-Amino-1-Boc-piperidine in a hydroxide solution has been determined, providing valuable insights into its binding interactions with the CCR5 receptor. This structural information is crucial for understanding the molecular basis of its inhibitory activity and for the design of more potent and selective CCR5 inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 87120-72-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,1,2 and 0 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 87120-72:
(7*8)+(6*7)+(5*1)+(4*2)+(3*0)+(2*7)+(1*2)=127
127 % 10 = 7
So 87120-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7,11H2,1-3H3/p+1

87120-72-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Amino-1-Boc-piperidine

1.2 Other means of identification

Product number -
Other names tert-butyl 4-aminopiperidine-1-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:87120-72-7 SDS

87120-72-7Synthetic route

4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester
206273-87-2

4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethanol under 5320.36 Torr;98%
With hydrogen; palladium 10% on activated carbon In ethanol98%
With hydrogen; palladium on activated charcoal In methanol
tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate
150008-24-5

tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With hydrogen; Raney nickel In ethanol under 2585.81 Torr;98%
With Raney nickel In methanol at 20℃; for 4h;83%
With hydrogen; 5% rhodium on activated aluminium oxide In methanol at 50℃;
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With hydroxylamine hydrochloride; sodium carbonate In water at 23℃; for 14h;
Stage #2: With hydrogen; Raney Ni In ethanol under 2585.81 Torr; for 3.5h; Solid phase;
96%
In ammonia-saturated methanol; aluminum nickel95.4%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With titanium(IV) isopropylate; ammonia In ethanol at 25℃; for 6h;
Stage #2: With sodium tetrahydroborate In ethanol at 25℃; for 3h; Further stages.;
88%
C18H24F3N3O2

C18H24F3N3O2

A

1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

B

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium chlorideA n/a
B 90%
C18H24F3N3O2

C18H24F3N3O2

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With chloro-trimethyl-silane; lithium chloride In N,N-dimethyl-formamide at 60℃; for 12h;90%
4-aminopiperidine
13035-19-3

4-aminopiperidine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Stage #1: 4-aminopiperidine; di-tert-butyl dicarbonate In 4-methyl-2-pentanone at 0 - 20℃; for 0.5h; Inert atmosphere; Reflux;
Stage #2: With water In isopropyl alcohol at 50℃;
85%
In dichloromethane at 0℃; for 5h;71.9%
Stage #1: 4-aminopiperidine With benzaldehyde In toluene for 3h; Heating / reflux;
Stage #2: di-tert-butyl dicarbonate In toluene at 20℃;
With triethylamine In 1,4-dioxane; water
With triethylamine In 1,4-dioxane; water
tert-butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate
153198-06-2

tert-butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 2h; Heating;81%
With ammonium hydroxide In methanol for 6h; Heating;5.75 g
With sodium bicarbonate; potassium carbonate In methanol
tert-butyl 4-[(2,4-dimethoxyphenyl)methylamino]piperidine-1-carboxylate

tert-butyl 4-[(2,4-dimethoxyphenyl)methylamino]piperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 25℃; for 16h;81%
1,1-dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate
873088-90-5

1,1-dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide In tetrahydrofuran; ethanol at 23℃; under 760.051 Torr; for 6h; Inert atmosphere;77%
tert-butyl 4-azidopiperidine-1-carboxylate
180695-80-1

tert-butyl 4-azidopiperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With ammonium hydroxide; triphenylphosphine In 1,4-dioxane; methanol at 27 - 28℃; for 0.5h;44%
With hydrogen; palladium on activated charcoal In methanol under 2068.59 Torr;
palladium-carbon In methanol
palladium-carbon In methanol; hexane; ethyl acetate
4-(benzylidene-amino)-piperidine-1-carboxylic acid tert-butyl ester
1044183-50-7

4-(benzylidene-amino)-piperidine-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With acetic acid for 48h;160 mg
With potassium hydrogensulfate for 1.5h;4.76 g
With sodium hydrogen sulfate; water for 2h;
With potassium hydrogensulfate; water In tert-butyl methyl ether at 20℃; for 4h; Inert atmosphere;6.0 g
N-phenylmethylidenepiperidinyl-4-amine
1029643-92-2

N-phenylmethylidenepiperidinyl-4-amine

A

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

B

(polystyrene-BAL)-NH-CH2-C6H4-p-NO2

(polystyrene-BAL)-NH-CH2-C6H4-p-NO2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 12 h / 25 °C
2: 4.76 g / aq. KHSO4 / 1.5 h
View Scheme
4-aminopiperidine
13035-19-3

4-aminopiperidine

A

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

B

(polystyrene-BAL)-NH-CH2-C6H4-p-NO2

(polystyrene-BAL)-NH-CH2-C6H4-p-NO2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / 4 h / Heating
2: toluene / 12 h / 25 °C
3: 4.76 g / aq. KHSO4 / 1.5 h
View Scheme
N-phenylmethylidenepiperidinyl-4-amine
1029643-92-2

N-phenylmethylidenepiperidinyl-4-amine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / 48 h / 20 °C
2: 160 mg / aq. AcOH / 48 h
View Scheme
Multi-step reaction with 2 steps
1: toluene / 14.08 h / 0 - 20 °C / Inert atmosphere
2: potassium hydrogensulfate; water / tert-butyl methyl ether / 4 h / 20 °C / Inert atmosphere
View Scheme
4-aminopiperidine
13035-19-3

4-aminopiperidine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Na2SO4 / CH2Cl2 / 24 h / 20 °C
2: Et3N / CH2Cl2 / 48 h / 20 °C
3: 160 mg / aq. AcOH / 48 h
View Scheme
Multi-step reaction with 3 steps
1: toluene / 5.5 h / Inert atmosphere; Reflux
2: toluene / 14.08 h / 0 - 20 °C / Inert atmosphere
3: potassium hydrogensulfate; water / tert-butyl methyl ether / 4 h / 20 °C / Inert atmosphere
View Scheme
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

A

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

B

4-pyrimidinyl-halide

4-pyrimidinyl-halide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaHB(OAc)3 / 1,2-dichloro-ethane
2: H2 / Pd/C / methanol
View Scheme
4-amino-1-benzylpiperidine
50541-93-0

4-amino-1-benzylpiperidine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / Et3N / CH2Cl2 / 12 h / 20 °C
2: H2 / Pd(OH)2/C / methanol / 12 h / 2585.81 Torr
3: CH2Cl2 / 6 h
4: 5.75 g / aq. NH3 / methanol / 6 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 94 percent / Et3N / CH2Cl2 / 0.25 h / 0 °C
2: H2 / Pearlman's catalyst / methanol / 48 h / 3102.9 Torr
3: 82 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
4: 81 percent / 37percent aq. NH4OH / methanol / 2 h / Heating
View Scheme
4-trifluoromethylcarbonylamino piperidine
97181-51-6

4-trifluoromethylcarbonylamino piperidine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 6 h
2: 5.75 g / aq. NH3 / methanol / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 82 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
2: 81 percent / 37percent aq. NH4OH / methanol / 2 h / Heating
View Scheme
N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoroacetamide
97181-50-5

N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoroacetamide

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / Pd(OH)2/C / methanol / 12 h / 2585.81 Torr
2: CH2Cl2 / 6 h
3: 5.75 g / aq. NH3 / methanol / 6 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: H2 / Pearlman's catalyst / methanol / 48 h / 3102.9 Torr
2: 82 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
3: 81 percent / 37percent aq. NH4OH / methanol / 2 h / Heating
View Scheme
4-bromo-1H-piperidine
90633-18-4

4-bromo-1H-piperidine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: DIPEA / CH2Cl2
2: NaN3 / dimethylformamide / 20 °C
3: H2 / 10 percent Pd/C / methanol / 2068.59 Torr
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: DIPEA / CH2Cl2
2: NaN3 / dimethylformamide / 20 °C
3: H2 / 10 percent Pd/C / methanol / 2068.59 Torr
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 16 h / 20 °C
2: palladium on activated charcoal; ammonia; hydrogen / methanol / 20 °C
View Scheme
tert-butyl 4-bromo-1-piperidinecarboxylate
180695-79-8

tert-butyl 4-bromo-1-piperidinecarboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaN3 / dimethylformamide / 20 °C
2: H2 / 10 percent Pd/C / methanol / 2068.59 Torr
View Scheme
H2 NOH.HCl

H2 NOH.HCl

water
7732-18-5

water

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

sodium carbonate
497-19-8

sodium carbonate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
In tetrahydrofuran; EtOH (abs); ethanol
In tetrahydrofuran; EtOH (abs); ethanol
H2 NOH HCl

H2 NOH HCl

water
7732-18-5

water

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

sodium carbonate
497-19-8

sodium carbonate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
In tetrahydrofuran; EtOH (abs); ethanol
In tetrahydrofuran
In tetrahydrofuran; EtOH (abs); ethanol
H2NOH HCl

H2NOH HCl

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water
C17H24N2O2

C17H24N2O2

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Stage #1: C17H24N2O2 With potassium hydrogensulfate In water for 1.5h;
Stage #2: With potassium hydroxide In water pH=10;
4-aminopiperidine
13035-19-3

4-aminopiperidine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

benzaldehyde
100-52-7

benzaldehyde

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Stage #1: 4-aminopiperidine; benzaldehyde In toluene for 3h; Heating / reflux;
Stage #2: di-tert-butyl dicarbonate In toluene at 20℃;
piperidin-4-one
41661-47-6

piperidin-4-one

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 16 h / 20 °C
2: palladium on activated charcoal; ammonia; hydrogen / methanol / 20 °C
View Scheme
2-benzthiazole thioacetic acid
6295-57-4

2-benzthiazole thioacetic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

N-(1-tert-butoxycarbonylpiperidin-4-yl)-(2-benzothiazolylthio)acetamide
701236-99-9

N-(1-tert-butoxycarbonylpiperidin-4-yl)-(2-benzothiazolylthio)acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 20h;100%
2-chloro-4,6-dimethoxy-1 ,3,5-triazine
3140-73-6

2-chloro-4,6-dimethoxy-1 ,3,5-triazine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester
951004-60-7

4-(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In acetonitrile at 160℃; for 0.333333h; microwave irradiation;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

(2-formylthiophen-3-yl)carbamic acid ethyl ester
122805-79-2

(2-formylthiophen-3-yl)carbamic acid ethyl ester

2-[[[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]amino]methyl]-3-(ethoxycarbonylamino)-thiophene

2-[[[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]amino]methyl]-3-(ethoxycarbonylamino)-thiophene

Conditions
ConditionsYield
100%
2,4-dinitrobenzenesulfonyl chloride
1656-44-6

2,4-dinitrobenzenesulfonyl chloride

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-{[(2,4-dinitrophenyl)sulfonyl]amino}piperidine-1-carboxylate
812690-24-7

tert-butyl 4-{[(2,4-dinitrophenyl)sulfonyl]amino}piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dinitrobenzenesulfonyl chloride; 1-(tert-butoxycarbonyl)-4-aminopiperidine With lutidine In dichloromethane at 0 - 20℃; for 18.5h;
Stage #2: With potassium hydrogensulfate; water for 0.5h; pH=2.5 - 3;
100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

2,4-dimethyl-1H-imidazole-5-carbaldehyde
68282-52-0

2,4-dimethyl-1H-imidazole-5-carbaldehyde

Tert-butyl 4-[(2,4-dimethylimidazol-5-yl)methylamino]piperidin-1-carboxylate

Tert-butyl 4-[(2,4-dimethylimidazol-5-yl)methylamino]piperidin-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃; Cooling with ice;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

tert-butyl 4-(2-chloroacetamido)piperidine-1-carboxylate
865432-01-5

tert-butyl 4-(2-chloroacetamido)piperidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere;90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.5h;89%
2,4-dichlorothiazole-5-carboxaldehyde
92972-48-0

2,4-dichlorothiazole-5-carboxaldehyde

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-{[(2,4-dichloro-thiazol-5-yl)methyl]-amino}-piperidine-1-carboxylic acid t-butyl ester
866329-10-4

4-{[(2,4-dichloro-thiazol-5-yl)methyl]-amino}-piperidine-1-carboxylic acid t-butyl ester

Conditions
ConditionsYield
Stage #1: 2,4-dichlorothiazole-5-carboxaldehyde; 1-(tert-butoxycarbonyl)-4-aminopiperidine With acetic acid In 1,2-dichloro-ethane at 21 - 26℃; for 1.5h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20 - 27℃; for 4.46667h;
100%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 18h;62%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

2,5(4)-dimethyl-1H-imidazole-4(5)-carboxaldehyde
68282-52-0

2,5(4)-dimethyl-1H-imidazole-4(5)-carboxaldehyde

tert-butyl 4-{[(2,4-dimethyl-1H-imidazol-5-yl)methyl]amino}piperidine-1-carboxylate
701298-75-1

tert-butyl 4-{[(2,4-dimethyl-1H-imidazol-5-yl)methyl]amino}piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In methanol at 20℃; for 2h;100%
Stage #1: 1-(tert-butoxycarbonyl)-4-aminopiperidine; 2,5(4)-dimethyl-1H-imidazole-4(5)-carboxaldehyde With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 15h;
Stage #2: With water; potassium carbonate
100%
4-chloro-2-fluoro-nitrobenzene
700-37-8

4-chloro-2-fluoro-nitrobenzene

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-((5-chloro-2-nitrophenyl)amino)piperidine-1-carboxylate
932700-82-8

tert-butyl 4-((5-chloro-2-nitrophenyl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;100%
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 18h;93.2%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃; for 1h;
With potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;
4-fluoro-2-methyl-5-nitro-benzonitrile
932375-18-3

4-fluoro-2-methyl-5-nitro-benzonitrile

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

1,1-dimethylethyl 4-[(4-cyano-5-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate
932375-19-4

1,1-dimethylethyl 4-[(4-cyano-5-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃;100%
4-fluoro-3-nitrobenzonitrile
1009-35-4

4-fluoro-3-nitrobenzonitrile

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-((4-cyano-2-nitrophenyl)amino)piperidine-1-carboxylate
320406-05-1

tert-butyl 4-((4-cyano-2-nitrophenyl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 72h;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 27℃; Cooling with ice;
methyl 2,4-difluoro-5-nitrobenzoate
125568-71-0

methyl 2,4-difluoro-5-nitrobenzoate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-{[5-fluoro-4-(methoxycarbonyl)-2-nitrophenyl]amino}piperidine-1-carboxylate
1037833-97-8

tert-butyl 4-{[5-fluoro-4-(methoxycarbonyl)-2-nitrophenyl]amino}piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 72h;100%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-((4-methylphenyl)methyl)aminopiperidine carboxylate
359877-52-4

tert-butyl 4-((4-methylphenyl)methyl)aminopiperidine carboxylate

Conditions
ConditionsYield
Stage #1: 4-methyl-benzaldehyde; 1-(tert-butoxycarbonyl)-4-aminopiperidine In ethanol for 4h; Reflux;
Stage #2: With sodium tetrahydroborate; ethanol at 20℃; for 24h;
100%
Stage #1: 4-methyl-benzaldehyde; 1-(tert-butoxycarbonyl)-4-aminopiperidine In ethanol for 4h; Heating / reflux;
Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 24h;
Stage #3: With water In ethanol
100%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

2-methylimidazole-4(5)-carbaldehyde
35034-22-1

2-methylimidazole-4(5)-carbaldehyde

tert-butyl4-{[(2-methyl-1H-imidazol-5-yl)methyl]amino}piperidine-1-carboxylate
1034411-58-9

tert-butyl4-{[(2-methyl-1H-imidazol-5-yl)methyl]amino}piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In methanol at 20℃; for 2h;100%
3-(Trifluoromethyl)benzenesulfonyl chloride
777-44-6

3-(Trifluoromethyl)benzenesulfonyl chloride

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-(3-trifluoromethylbenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester
884308-82-1

4-(3-trifluoromethylbenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 2h;100%
4,6-bis-benzyloxy-5'-isopropyl-2'-methoxybiphenyl-3-carboxylic acid
1143624-55-8

4,6-bis-benzyloxy-5'-isopropyl-2'-methoxybiphenyl-3-carboxylic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-[(4,6-bis-benzyloxy-5'-isopropyl-2'-methoxybiphenyl-3-carbonyl)amino]piperidine-1-carboxylic acid tert-butyl ester
1143624-64-9

4-[(4,6-bis-benzyloxy-5'-isopropyl-2'-methoxybiphenyl-3-carbonyl)amino]piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

3,5-ditrifluoromethylisocyanate
16588-74-2

3,5-ditrifluoromethylisocyanate

tert-butyl 4-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)piperidine-1-carboxylate
1275064-22-6

tert-butyl 4-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)piperidine-1-carboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

4-(4-nitrobenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester
1233952-63-0

4-(4-nitrobenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
N-(6-chloro-4-((cis-2,6-dimethylmorpholino)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine
1365839-19-5

N-(6-chloro-4-((cis-2,6-dimethylmorpholino)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

1,1-dimethylethyl 4-{[4-{[cis-2,6-dimethyl-4-morpholinyl]methyl}-6-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)-2-pyridinyl]amino}-1-piperidinecarboxylate
1365839-20-8

1,1-dimethylethyl 4-{[4-{[cis-2,6-dimethyl-4-morpholinyl]methyl}-6-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)-2-pyridinyl]amino}-1-piperidinecarboxylate

Conditions
ConditionsYield
With lithium hexamethyldisilazane; (NHC)Pd(allyl)Cl In tetrahydrofuran at 80℃; for 1h; Microwave irradiation; Inert atmosphere;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

2,4-dibromobutanoyl chloride
82820-87-9

2,4-dibromobutanoyl chloride

tert-butyl 4-(2,4-dibromobutanamido)piperidin-1-carboxylate
1365998-53-3

tert-butyl 4-(2,4-dibromobutanamido)piperidin-1-carboxylate

Conditions
ConditionsYield
Stage #1: 1-(tert-butoxycarbonyl)-4-aminopiperidine; 2,4-dibromobutanoyl chloride With triethylamine In dichloromethane at 0℃;
Stage #2: With sodium hydrogencarbonate In dichloromethane Product distribution / selectivity;
100%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;
1-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine
1245649-52-8

1-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-(1-benzenesulphonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4ylamino)piperidine-1-carboxylic acid tert-butyl ester
1315495-05-6

4-(1-benzenesulphonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4ylamino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 2h; Reflux;100%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol Inert atmosphere; Heating;
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

4-(3-cyano-propylamino)-piperidine-1-carboxylic acid tert-butyl ester

4-(3-cyano-propylamino)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 48h; Reflux;100%
3-(6-chloropyridin-3-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole

3-(6-chloropyridin-3-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

1-(5-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)pyridin-2-yl)piperidin-4-amine

1-(5-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)pyridin-2-yl)piperidin-4-amine

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 180℃; for 2h; Time; Microwave irradiation;100%
4-((4-(4-(trifluoromethoxy)phenyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoic acid

4-((4-(4-(trifluoromethoxy)phenyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

N-(1-Boc-4-piperidyl)-4-((4-(6-(trifluoromethoxy)pyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

N-(1-Boc-4-piperidyl)-4-((4-(6-(trifluoromethoxy)pyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;100%
1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

5,7-dichloropyrazolo[1,5-a]pyrimidine
57489-77-7

5,7-dichloropyrazolo[1,5-a]pyrimidine

tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate

tert-butyl 4-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 100℃; for 12h;100%
With triethylamine In acetonitrile at 100℃; for 12h;
4-((4-(6-methoxy-3-pyridyl)-5-trifluoromethylpyrimidin-2-yl)amino)benzoic acid

4-((4-(6-methoxy-3-pyridyl)-5-trifluoromethylpyrimidin-2-yl)amino)benzoic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-(4-{[4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzamido)piperidine-1-carboxylate

tert-butyl 4-(4-{[4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzamido)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h;100%
2-(4-chloro-3-fluorophenoxy)acetic acid
331-41-9

2-(4-chloro-3-fluorophenoxy)acetic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-[[2-(4-chloro-3-fluorophenoxy)acetyl]amino]piperidine-1-carboxylate

tert-butyl 4-[[2-(4-chloro-3-fluorophenoxy)acetyl]amino]piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2-(4-chloro-3-fluorophenoxy)acetic acid; 1-(tert-butoxycarbonyl)-4-aminopiperidine With HATU In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
100%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 12h;
6-chloro-2-quinolinecarboxylic acid
59394-30-8

6-chloro-2-quinolinecarboxylic acid

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-[(6-chloroquinoline-2-carbonyl)amino]piperidine-1-carboxylate

tert-butyl 4-[(6-chloroquinoline-2-carbonyl)amino]piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 6-chloro-2-quinolinecarboxylic acid; 1-(tert-butoxycarbonyl)-4-aminopiperidine With HATU In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
100%
N-(2,4-dimethoxybenzyl)-5-fluoro-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide

N-(2,4-dimethoxybenzyl)-5-fluoro-N-(6-fluoropyridin-2-yl)-4-(trifluoromethyl)pyridine-2-sulfonamide

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

tert-butyl 4-((6-(N-(2,4-dimethoxybenzyl)-N-(6-fluoropyridin-2-yl)sulfamoyl)-4-(trifluoromethyl)pyridin-3-yl)amino)piperidine-1-carboxylate

tert-butyl 4-((6-(N-(2,4-dimethoxybenzyl)-N-(6-fluoropyridin-2-yl)sulfamoyl)-4-(trifluoromethyl)pyridin-3-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 70℃; for 2h;100%

87120-72-7Relevant articles and documents

sEH Inhibitor or pharmaceutically acceptable composition thereof as well as preparation method and application thereof

-

Paragraph 0117; 0119, (2021/09/21)

The invention provides sEH inhibitor or a pharmaceutically acceptable composition and a preparation method and application thereof, and belongs to the technical field of medicines. sEH Inhibitor or a pharmaceutically acceptable composition thereof according to the present invention is provided, and the sEH inhibitor has the structure shown I. sEH Inhibitor provided by the invention can stabilize an endogenous substance epoxy fatty acid with wide physiological activity, has a strong inhibition effect on human recombinant sEH, and can be used for regulating the generation of a plurality of pro-inflammatory cytokines. The invention relieves the stress of endoplasmic reticulum, prevents or reverses the dysfunction of endothelial dysfunction, stabilizes mitochondria function multiple action mechanisms to obviously relieve neuropathic pain, and can effectively avoid adverse reactions related to the target spot. Furthermore, the sEH inhibitor structure provided by the invention does not contain free carboxyl groups, can avoid adverse reactions such as gastrointestinal irritation caused by oral administration, and is small in adverse reaction, high in bioavailability, excellent in analgesic effect and small in administration amount.

Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer

Barthelemy, Anne-Laure,Douglas, James J.,Górski, Bartosz,Juliá, Fabio,Leonori, Daniele

, p. 623 - 630 (2021/07/25)

Despite the fact that nucleophilic displacement (SN2) of alkyl halides with nitrogen nucleophiles is one of the first reactions introduced in organic chemistry teaching, its practical utilization is largely limited to unhindered (primary) or ac

PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES

-

Page/Page column 38, (2020/12/30)

The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.