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

Chemical Properties

WHITE TO YELLOWISH CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 4727-72-4 differently. You can refer to the following data:
1. A piperidine based pesticide
2. 1-Benzyl-4-hydroxypiperidine is the reactant for synthesis of: Muscarinic acetylcholine receptor antagonist and beta 2 adrenoceptor agonist1 Fatty acid amide hydrolase inhibitors PI3 kinase-alpha inhibitors Flavonoid derivatives used as dual binding acetylcholinesterase inhibitors Urotensin-II receptor antagonists Rho kinase inhibitors.
3. 1-Benzyl-4-hydroxypiperidine was used as an alternative molecule to study the ligand concentration attached to the epoxy-activated Sepharose 6B.

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 
• 2905-56-8 N-Benzylpiperidine 
• 3046-49-9 [14C]formaldehyde 
• 17150-62-8 N-benzyl-3-butenylamine 
• 50-00-0 formaldehyd 
• 111865-51-1 N-[1-(4-methoxyphenyl)-3-butenyl]benzylamine 
• 111865-50-0 benzyl[1-(4-methylphenyl)but-3-enyl]amine 
• 99948-39-7 ethyl 2-(benzylamino)pent-4-enoate 
• 173416-02-9 (E)-N-benzyl-1-phenylhexa-1,5-dien-3-amine 
• 109-87-5 Dimethoxymethane 
• 88381-98-0 N-(1-phenyl-3-butenyl)benzylamine 
• 111865-49-7 N-benzyl-1-(4-chlorophenyl)-3-butenylamine 

Downstream Products

• 126799-57-3 1-Benzyl-4-(4-(methylthio)phenoxy)piperidine 
• 118108-61-5 1-benzylpiperidin-4-yl 2-hydroxy-2,2-diphenylacetate 
• 126799-56-2 1-Benzyl-4-(2-(methylthio)phenoxy)piperidine 
• 751430-77-0 <<1-(phenylmethyl)-4-piperidinyl>oxy>acetic acid 
• 127806-47-7 1-benzyl-4-(2-pyridyloxy)piperidine 
• 94886-07-4 1-benzylpiperidin-4-yl acetate 
• 67848-71-9 4-chloro-1-benzylpiperidine 
• 558462-66-1 4-[(1-Benzylpiperidin-4-yl)(4-chlorophenylsulfonyl)methyl]pyridine 
• 863249-61-0 2,2-dimethyl-propionic acid 1-benzyl-piperidin-4-yl ester 
• 171722-92-2 4-piperidyl N-(2-biphenyl)carbamate 
• 900511-87-7 3-[(1-benzylpiperidin-4-yl)oxy]-2-methyl-pyridine 
• 221087-81-6 2-(2,5-Dimethylpyrrolyl)-6(4-((N-benzyl)-4-piperidinyloxy)-naphth-1-yl)pyridine 
• 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 

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.