120938-72-9

Usage

Class

Chemical compound

Potential use

Pharmaceutical intermediate or precursor

Derivative

Piperidine

Contains

Cyclohexyl and hydroxyphenyl groups

Structure

Suggests potential biological activity

Interest

Development of new medications

Safety

Handle with caution, follow all necessary safety protocols and regulations.

InChI:InChI=1/C22H35NO2/c1-17-16-23(13-11-21(25)18-7-4-3-5-8-18)14-12-22(17,2)19-9-6-10-20(24)15-19/h6,9-10,15,17-18,21,24-25H,3-5,7-8,11-14,16H2,1-2H3

Upstream product

• 132621-42-2 (-)-(1S)-1-(tert-Butyldimethylsiloxy)-1-cyclohexyl-3-hydroxypropane 
• 312329-70-7 4-(3-hydroxyphenyl)-trans-3,4-dimethylpiperidine 
• 172376-41-9 (S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate 
• 145678-87-1 (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 119193-19-0 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol 
• 123001-07-0 (-)-(1R)-1-Hydroxy-1-cyclohexyl-2-propene 
• 149655-33-4 (3R,4R)-4-(3-methoxyphenyl)-3,4-dimethylpiperidine 
• 132621-49-9 (-)-(1R)-1-(tert-Butyldimethylsiloxy)-1-cyclohexyl-2-propene 
• 4352-44-7 1-cyclohexylprop-2-en-1-ol 
• 143919-34-0 (3R,5R)-1,3,4-trimethyl-4-<3-(1-methylethoxy)phenyl>piperidine 
• 145678-86-0 (3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester 
• 132697-07-5 (+)-1,3(R),4(R)-Trimethyl-4-(3-methoxyphenyl)piperidine 

Relevant academic research and scientific papers

Treatment of pruritus

The use of certain known 1,3,4 trisubstituted 4-aryl-piperidines for the treatment of pruritus in humans and animals is disclosed.

Synthesis of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists: Application of the cis-thermal elimination of carbonates to alkaloid synthesis

Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3-dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyridine 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190°C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydropyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.

3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: Opioid Antagonists with Potent Anorectant Activity

A series of (3R*,4R*)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists with varying substituents on the nitrogen were evaluated for either effect on food consumption in obese Zucker rats.Opioid affinity (μ, κ, and δ for

PIPERIDINE OPIOID ANTAGONISTS

This invention provides trans-3,4 1-substituted-3-substituted-4-methyl-4-(3-substituted phenyl)piperidines as opioid antagonists capable of blocking the mu or kappa receptors in the brain.