143919-34-0

Basic information

• Product Name: Piperidine, 1,3,4-triMethyl-4-[3-(1-Methylethoxy)phenyl]-, (3R,4R)-
• Synonyms: Piperidine, 1,3,4-triMethyl-4-[3-(1-Methylethoxy)phenyl]-, (3R,4R)-
• CAS NO: 143919-34-0
• Molecular Formula: C₁₇H₂₇NO
• Molecular Weight: 261.40238
• Mol File: 143919-34-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Piperidine, 1,3,4-triMethyl-4-[3-(1-Methylethoxy)phenyl]-, (3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1,3,4-triMethyl-4-[3-(1-Methylethoxy)phenyl]-, (3R,4R)-(143919-34-0)
• EPA Substance Registry System: Piperidine, 1,3,4-triMethyl-4-[3-(1-Methylethoxy)phenyl]-, (3R,4R)-(143919-34-0)

Safety Data

• Hazardous Substances Data: 143919-34-0(Hazardous Substances Data)

Upstream product

• 149541-62-8 C₁₉H₂₉NO₄ 
• 149541-62-8 cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 143919-32-8 (R)-1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine 

Downstream Products

• 145678-86-0 (3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester 
• 156130-41-5 ADL 08-0011 
• 145603-86-7 (+)-<<2'(S)-<<4(R)-3-(hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl>methyl>-1-oxo-3-phenylpropyl>amino>acetic acid 2-methylpropyl ester 
• 156053-89-3 Entereg 
• 156130-44-8 2‐((R)‐2‐benzyl‐3‐((3R,4R)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 
• 1184775-81-2 C₁₇H₂₇NO*C₂₀H₁₈O₈ 
• 170098-29-0 methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate 
• 170098-39-2 methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate 
• 119193-09-8 (+)-1-(3(S)-3-hydroxy-3-cyclohexylpropyl)-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 119193-19-0 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol 

Relevant articles and documents

Synthesis and characterization of all possible diastereoisomers of alvimopan

Isolation of all possible diastereomers of alvimopan 1 was found to be challenging. In order to perform cut off studies during analytical method development, it was mandatory to synthesize and characterize all the diastereomeric impurities. Here in, our efforts toward the synthesis and isolation of alvimopan (1) diastereomers are discussed.

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.

Preparation of substituted tetrahydropyridines

A process for preparing certain 1,3,4,4-tetrasubstituted-1,2,3,4-tetrahydropyridines is provided as well as certain 4-carbonate-1,3,4-trisubstituted-piperidines.