trans N-Benzyl Paroxetine

Base Information

• Chemical Name: trans N-Benzyl Paroxetine
• CAS No.: 105813-14-7
• Molecular Formula: C26H26 F N O3
• Molecular Weight: 419.496
• UNII: MLV7RU9XDD
• DSSTox Substance ID: DTXSID401123259
• Nikkaji Number: J2.113.869J
• Mol file: 105813-14-7.mol

Synonyms:trans N-Benzyl Paroxetine;105813-14-7;(-)-N-Benzylparoxetine;N-Benzylparoxetine;MLV7RU9XDD;(3S,4R)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-1-benzyl-4-(4-fluorophenyl)piperidine;(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-1-benzyl-4-(4-fluorophenyl)piperidine;Piperidine,3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-(phenylmethyl)-,(3S,4R)-;(3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-1-benzyl-4-(4-fluorophenyl)piperidine;Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(phenylmethyl)-, (3S,4R)-;Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(phenylmethyl)-, trans-(-)-;starbld0017939;UNII-MLV7RU9XDD;SCHEMBL7240803;AGTKMLMRHVWXHN-URXFXBBRSA-N;DTXSID401123259;Paroxetine Hydrochloride Anhydrous EP Impurity C;J-001485;(-)-trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine;(-)trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine;(3S,4R)-1-Benzyl-3-[(1,3-benzodioxole-5-yl)oxymethyl]-4-(4-fluorophenyl)piperidine;(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-(phenylmethyl)piperidine;N-Benzyl Paroxetine;(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-(phenylmethyl)-piperidine

Chemical Property of trans N-Benzyl Paroxetine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Boiling Point: 527.005°C at 760 mmHg
• Flash Point: 272.523°C
• PSA: 30.93000
• Density: 1.216g/cm³
• LogP: 5.17700
• Storage Temp.: Refrigerator
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 419.18967185
• Heavy Atom Count: 31
• Complexity: 549

Purity/Quality:

99.9% ^*data from raw suppliers

transN-BenzylParoxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC(C1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4)CC5=CC=CC=C5
• Isomeric SMILES: C1CN(C[C@H]([C@@H]1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4)CC5=CC=CC=C5
• Uses: Paroxetine intermediate

Technology Process of trans N-Benzyl Paroxetine

There total 12 articles about trans N-Benzyl Paroxetine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

benzyl bromide (100-39-0) + (-)-paroxetine hydrochloride (110429-35-1,130855-30-0) → (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine (105813-14-7)

Guidance literature:

With potassium carbonate; In acetonitrile; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.9b08662

Reference yield: 68.0%

Sesamol (533-31-3) + Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester (201855-71-2) → C26H26FNO3 + (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine (105813-14-7)

Guidance literature:

Sesamol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.333333h; Inert atmosphere;

Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester; In N,N-dimethyl-formamide; mineral oil; at 90 ℃; for 15h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201603056

Reference yield: 52.0%

Sesamol (533-31-3) + Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester (201855-71-2) → (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine (105813-14-7)

Guidance literature:

Sesamol; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;

Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester; In N,N-dimethyl-formamide; at 90 ℃; for 14h;

DOI:10.1039/b617260a

upstream raw materials:

Sesamol

Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

Downstream raw materials:

paroxetine

Refernces

• 1、 Chang, Yejin,Yesilcimen, Ahmet,Cao, Min,Zhang, Yuyang,Zhang, Bochao,Chan, Jessica Z.,Wasa, Masayuki. "Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C-H Bonds of Drug Molecules". supporting information. p. 14570 - 14575. Retrieved 2019/10/11.
• 2、 ?íhalová, Sylva,Valero, Guillem,Schimer, Ji?í,Humpl, Marek,Dra?ínsky, Martin,Moyano, Albert,Rios, Ramon,Vesely, Jan. "Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines". scheme or table. p. 8942 - 8950. Retrieved 2011/12/01.