4727-72-4

Basic information

• Product Name: 1-Benzyl-4-hydroxypiperidine
• Synonyms: 4-HYDROXY-1-BENZYLPIPERIDINE;benzyl-4-piperidinol;4-Piperidinol, 1-(phenylmethyl)-;1-Benzyl-4-hydroxypiperidine,97%;NSC 72991;1-(Phenylmethyl)-4-piperidinol;1-Benzyl-piperidin-4-ol;4-Piperidinol, 1-benzyl-
• CAS NO: 4727-72-4
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• EINECS: 225-226-9
• Product Categories: Alcohols and Derivatives;Non-Chiral heterocyclic compounds;Agro-Products;Aromatics;Heterocycles;Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 4727-72-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 127-128 °C2 mm Hg(lit.)
• Flash Point: 121-123°C/0.7mm
• Appearance: White to yellow/Crystalline Powder
• Density: 1.0096 (rough estimate)
• Vapor Pressure: 0.000738mmHg at 25°C
• Refractive Index: 1.5212 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 14.87±0.20(Predicted)
• Sensitive: Hygroscopic
• BRN: 146118
• CAS DataBase Reference: 1-Benzyl-4-hydroxypiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-4-hydroxypiperidine(4727-72-4)
• EPA Substance Registry System: 1-Benzyl-4-hydroxypiperidine(4727-72-4)

Safety Data

• Hazard Codes: T,C,Xi,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 26-45-37/39-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 4727-72-4(Hazardous Substances Data)

Usage

Description

1-Benzyl-4-hydroxypiperidine is a white to yellowish crystalline powder with a chemical structure that features a piperidine ring with a benzyl group at the first position and a hydroxyl group at the fourth position. It is a versatile chemical intermediate with a wide range of applications in various industries.

Uses

1-Benzyl-4-hydroxypiperidine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, including:
Muscarinic acetylcholine receptor antagonists and beta 2 adrenoceptor agonists, which are used in the treatment of respiratory diseases and other conditions.
Fatty acid amide hydrolase inhibitors, which have potential therapeutic applications in pain management and neurodegenerative disorders.
PI3 kinase-alpha inhibitors, which are being investigated for their potential role in cancer treatment.
Flavonoid derivatives used as dual binding acetylcholinesterase inhibitors, which may have applications in the treatment of Alzheimer's disease and other cognitive disorders.
Urotensin-II receptor antagonists, which could be useful in the treatment of cardiovascular diseases.
Rho kinase inhibitors, which have potential applications in the treatment of various conditions, including glaucoma and hypertension.
Additionally, 1-Benzyl-4-hydroxypiperidine is used as a reactant in the synthesis of a piperidine-based pesticide, which is employed in the agricultural industry to protect crops from pests.
In the field of research, 1-Benzyl-4-hydroxypiperidine is used as an alternative molecule to study the ligand concentration attached to the epoxy-activated Sepharose 6B, which is a type of affinity chromatography resin used for protein purification and immobilization.
Overall, 1-Benzyl-4-hydroxypiperidine is a valuable chemical intermediate with diverse applications in the pharmaceutical, agricultural, and research industries, making it an important compound for the development of new drugs and chemical products.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3512, 1986 DOI: 10.1021/ja00272a059

InChI:InChI=1/C12H17NO/c14-12-6-8-13(9-7-12)10-11-4-2-1-3-5-11/h1-5,12,14H,6-10H2/p+1

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 20821-52-7 1-benzyl-4-piperidone hydrochloride 
• 64-17-5 ethanol 
• 50-00-0 formaldehyd 
• 111865-49-7 N-benzyl-1-(4-chlorophenyl)-3-butenylamine 
• 88381-98-0 N-(1-phenyl-3-butenyl)benzylamine 
• 109-87-5 Dimethoxymethane 
• 173416-02-9 (E)-N-benzyl-1-phenylhexa-1,5-dien-3-amine 
• 99948-39-7 ethyl 2-(benzylamino)pent-4-enoate 
• 111865-50-0 benzyl[1-(4-methylphenyl)but-3-enyl]amine 
• 111865-51-1 N-[1-(4-methoxyphenyl)-3-butenyl]benzylamine 
• 3046-49-9 [14C]formaldehyde 

Downstream Products

• 94886-07-4 1-benzylpiperidin-4-yl acetate 
• 900512-07-4 1-benzyl-4-(2-chloro-phenoxy)piperidine 
• 262444-46-2 7-(1-benzyl-4-piperidyl)-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 288252-28-8 5-amino-2-(1-benzylpiperidine-4-yloxy)benzonitrile 
• 175203-64-2 3-(1-benzylpiperidin-4-yloxy)-propionitrile 
• 222400-98-8 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-benzylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 
• 108932-21-4 4-methyl-2-<<(4-methoxyphenyl)methyl>thio>-6-<2-(trifluoromethyl)phenyl>-1,5(6H)-pyrimidinedicarboxylic acid 5-ethyl 1-<1-(phenylmethyl)-4-piperidinyl> diester 
• 112734-21-1 4-bromo-2-nitro-benzoyl chloride 

Relevant articles and documents

COMPOUNDS AND METHODS OF USE

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein X1, X2, X3, X4, X5, A, L, R1, R2, R5, m and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Synthesis and Bio-Evaluation of N-Benzylpiperidine-8-Hydroxyquinoline Derivatives as Potential Cholinesterase Inhibitors, Metal Ion Chelators and Calcium Channel Blockers

Abstract: A new series of N-benzylpiperidine 8-hydroxyquinoline derivatives were synthesized and evaluated as cholinesterase inhibitors, metal ion chelators and calcium channel blockers. It was found that the ethyl cholinesterase inhibition activity could be improved when the linker between N-benzylpiperidine and 8?hydroxyquinoline groups were extended. Among all derivatives, compound (XIIId) showed best acetyl cholinesterase inhibition activity with an IC50 value of 0.24 ± 0.03 μM. It also showed metal ion chelating activity with a metal-compound ratio of 1 : 2 on copper or zinc ions. The calcium channel blocking property of select compounds were tested and compared by patching clamp on HEK293 cell expressing Cav1.2 calcium channel. Among tested compounds, cholinesterase inhibitor 8c showed mild calcium channel blockade activity with the inhibition ratio of calcium channel of 24.56 ± 2.44% (10 μM). This result suggested that the potential neuroprotective ability of this cholinesterase inhibitor might be partially related to the calcium channel blocking property.

N-alkylpiperidine carbamates as potential anti-Alzheimer's agents

Compounds capable of interacting with single or multiple targets involved in Alzheimer's disease (AD) pathogenesis are potential anti-Alzheimer's agents. In our aim to develop new anti-Alzheimer's agents, a series of 36 new N-alkylpiperidine carbamates was designed, synthesized and evaluated for the inhibition of cholinesterases [acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)] and monoamine oxidases [monoamine oxidase A (MAO-A and monoamine oxidase B (MAO-B)]. Four compounds are very promising: multiple AChE (IC50 = 7.31 μM), BChE (IC50 = 0.56 μM) and MAO-B (IC50 = 26.1 μM) inhibitor 10, dual AChE (IC50 = 2.25 μM) and BChE (IC50 = 0.81 μM) inhibitor 22, selective BChE (IC50 = 0.06 μM) inhibitor 13, and selective MAO-B (IC50 = 0.18 μM) inhibitor 16. Results of enzyme kinetics experiments showed that despite the carbamate group in the structure, compounds 10, 13, and 22 are reversible and non-time-dependent inhibitors of AChE and/or BChE. The resolved crystal structure of the complex of BChE with compound 13 confirmed the non-covalent mechanism of inhibition. Additionally, N-propargylpiperidine 16 is an irreversible and time-dependent inhibitor of MAO-B, while N-benzylpiperidine 10 is reversible. Additionally, compounds 10, 13, 16, and 22 should be able to cross the blood-brain barrier and are not cytotoxic to human neuronal-like SH-SY5Y and liver HepG2 cells. Finally, compounds 10 and 16 also prevent amyloid β1–42 (Aβ1–42)-induced neuronal cell death. The neuroprotective effects of compound 16 could be the result of its Aβ1–42 anti-aggregation effects.