214335-16-7

Basic information

• Product Name: (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester
• Synonyms: (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester;(3S,4S)-4-(4-Chlorophenyl)-1-methyl-3-piperidinecarboxylic acid methyl ester
• CAS NO: 214335-16-7
• Molecular Formula: C₁₄H₁₈ClNO₂
• Molecular Weight: 267.75
• Mol File: 214335-16-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 343.503°C at 760 mmHg
• Flash Point: 161.545°C
• Appearance: /
• Density: 1.157
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester(214335-16-7)
• EPA Substance Registry System: (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester(214335-16-7)

Safety Data

• Hazardous Substances Data: 214335-16-7(Hazardous Substances Data)

Usage

General Description

The chemical "(3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester" is a methyl ester derivative of a piperidine carboxylic acid compound. It is composed of a piperidine ring with a methyl and carboxylic acid group, as well as a chlorophenyl substituent. (3S,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylicacidmethylester has potential applications in the field of medicinal chemistry and drug development, as piperidine derivatives are known to exhibit a wide range of biological activities, including analgesic and anesthetic properties. Additionally, the presence of the chlorophenyl group may provide additional pharmacological activities or improve the compound's bioavailability. Further research is needed to fully understand the potential uses and effects of this chemical.

InChI:InChI=1/C14H18ClNO2/c1-16-8-7-12(13(9-16)14(17)18-2)10-3-5-11(15)6-4-10/h3-6,12-13H,7-9H2,1-2H3/t12-,13-/m1/s1

Upstream product

• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 205805-13-6 (±)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3β-carboxylate 
• 63-75-2 arecoline 

Downstream Products

• 214335-24-7 (-)-Methyl 1-Methyl-4β-phenylpiperidine-3β-carboxylate 
• 214335-19-0 (3S,4S)-4-(4-chlorophenyl)-3-(hydroxymethyl)-1-methylpiperidine 
• 263769-22-8 (+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate 
• 258827-05-3 (-)-Methyl 4β-(4-chlorophenyl)-piperidine-3β-carboxylate 
• 263769-24-0 (+)-4β-(4-Chlorophenyl)-3α-(hydroxymethyl)-1-methylpiperidine 
• 256375-14-1 2-{{3-[(3S,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidin-3-yl]-propyl}-[2-(4-methoxy-benzylsulfanyl)-ethyl]-amino}-N-[2-(4-methoxy-benzylsulfanyl)-ethyl]-acetamide 
• 256375-13-0 {3-[(3S,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidin-3-yl]-propyl}-[2-(4-methoxy-benzylsulfanyl)-ethyl]-amine 
• 747397-02-0 3-[(3S,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidin-3-yl]-propionic acid 
• 256375-11-8 (E)-3-[(3S,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidin-3-yl]-acrylic acid methyl ester 
• 214335-31-6 (3S,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidine-3-carbaldehyde 
• 258827-07-5 (3S,4S)-4-(4-Chloro-phenyl)-1-ethoxycarbonylmethyl-piperidine-3-carboxylic acid methyl ester 
• 258827-10-0 (1R,4S,5S)-4-(4-Chloro-phenyl)-1-aza-bicyclo[3.2.1]octan-6-one 
• 258827-13-3 (1S,4S,5R)-4-(4-Chloro-phenyl)-1-aza-bicyclo[3.2.1]octan-6-one 
• 263769-44-4 (+)-4β-(4-Chlorophenyl)-1-methylpiperidine-3α-carboxylic Acid 

Relevant articles and documents

Process development toward the pilot scale synthesis of the piperidine-based cocaine analogue and potent dopamine and norepinephrine reuptake inhibitor CTDP 31,446

(+)-Methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate hydrochloride (CTDP 31,446) is known as a dopamine reuptake inhibitor. This cocaine analogue lacking the tropane skeleton is being considered for potential treatment of cocaine addiction. Herein we report the development of a scalable process for the preparation of this compound. This study was mainly aimed at improving the process throughput, eliminating chromatographic purifications for the separation of (±)-6-cis isomer from (±)-6-trans isomer, and developing a robust crystallization for isolation of pure (±)-6-cis in a single crop with a good mass recovery. The process development work also highlights an efficient recycle of (±)-6-trans via a kinetic epimerization followed by crystallization of the resulting (±)-6-cis isomer. The resolution of (±)-6-cis and the crystallization of the final HCl salt were optimized and implemented to afford CTDP-31,446 with high purity and good mass recovery.

Analogs of cocaine

The invention provides a compound of formula (I): STR1wherein R 1, R 2, R 3, and Y have any of the meanings defined in the specification; as well a pharmaceutical composition comprising a compound of formula I; intermediates and methods useful for preparing a compound of formula I; and therapeutic methods for treating drug addiction, Parkinson''s disease or depression comprising administering a compound of formula I, to a mammal in need of such treatment.