176022-02-9

Basic information

• Product Name: 3R,4S-4-[phenyl-1-methylpiperidinyl] methanol
• Synonyms: 3R,4S-4-[phenyl-1-methylpiperidinyl] methanol;[(3R,4S)-4-Phenyl-1-methylpiperidinyl]methanol,99%e.e.
• CAS NO: 176022-02-9
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.29606
• Mol File: 176022-02-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3R,4S-4-[phenyl-1-methylpiperidinyl] methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3R,4S-4-[phenyl-1-methylpiperidinyl] methanol(176022-02-9)
• EPA Substance Registry System: 3R,4S-4-[phenyl-1-methylpiperidinyl] methanol(176022-02-9)

Safety Data

• Hazardous Substances Data: 176022-02-9(Hazardous Substances Data)

Upstream product

• 178634-04-3 (+)-trans-3-(4-hydroxyphenoxymethyl)-1-methyl-4-phenylpiperidine 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 59859-58-4 femoxetine 
• 54088-36-7 (+)-trans-3-(3,4-methylenedioxyphenoxymethyl)-4-phenylpiperidine hydrochloride 

Relevant articles and documents

Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines.

Synthesis and 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines

A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or α-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT2A and 5HT2C receptors. Acta Chemica Scandinavica 1996.