149541-62-8

Basic information

• Product Name: ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate
• Synonyms: ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate;Carbonic acid, 1,3-diMethyl-4-[3-(1-Methylethoxy)phenyl]-4-piperidinyl ethyl ester
• CAS NO: 149541-62-8
• Molecular Formula: C19H29NO4
• Molecular Weight: 335.43786
• Mol File: 149541-62-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 445.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• PKA: 7.22±0.10(Predicted)
• CAS DataBase Reference: ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate(149541-62-8)
• EPA Substance Registry System: ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate(149541-62-8)

Safety Data

• Hazardous Substances Data: 149541-62-8(Hazardous Substances Data)

Usage

General Description

Ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate is a chemical compound with a complex molecular structure. It is an ester derivative of piperidine, a heterocyclic amine. The presence of the isopropoxyphenyl group and the methyl substituents on the piperidine ring imparts specific chemical properties to the compound, making it potentially useful in pharmaceutical or agrochemical applications. However, due to its complex structure and potential reactivity, it should be handled and used with caution and under appropriate safety measures.

Upstream product

• 541-41-3 chloroformic acid ethyl 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 
• 172376-39-5 C₁₆H₂₅NO₂ 
• 591-20-8 3-Bromophenol 
• 172376-39-5 cis-(+/-)-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>-4-piperidinol 
• 172376-39-5 cis-(+/-)-1,3-dimethyl-4-[3-(1-methyl-ethoxy)phenyl]-4-piperidinol 

Downstream Products

• 143919-32-8 (R)-1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine 
• 444904-02-3 (S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine 
• 143919-34-0 (3R,5R)-1,3,4-trimethyl-4-<3-(1-methylethoxy)phenyl>piperidine 
• 223424-24-6 (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine 
• 1184775-81-2 C₁₇H₂₇NO*C₂₀H₁₈O₈ 
• 145678-86-0 (3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester 
• 119193-19-0 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol 
• 145678-87-1 (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 170098-39-2 methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate 
• 170098-29-0 methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate 
• 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 

Relevant articles and documents

Improved process for preparation of (3R,4R)-3-(3,4-dimethyl-4-piperidinyl) phenol, a key intermediate for the synthesis of alvimopan

This report discloses an industrially feasible and cost efficient process for the preparation of the compound [(3R, 4R)-3-(3,4-dimethyl-4-piperidinyl)- phenol] (1), which is used as the key intermediate for preparation of the opioid drug Alvimopan. The overall yield in this process is increased from 15 to 30%, mainly due to the improvement in yield from 26 to 53% for intermediate 7.

Compositions containing opioid antagonists

Compositions containing opioid antagonists are disclosed, particularly alvimopan and its active metabolite in solid dosage forms, where the drug is uniformly distributed, achieves the desired bioavailability, and is stable. Methods of preparing and using the compositions containing opioid antagonists are also disclosed. The results are achieved by a combination of processing techniques and component selection.

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.