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

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

Uses

Used in Pharmaceutical Applications:
Ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical properties, including the isopropoxyphenyl group and methyl substituents, make it a valuable building block in the development of new therapeutic agents.
Used in Agrochemical Applications:
In the agrochemical industry, ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate is used as a precursor for the synthesis of bioactive compounds. Its specific chemical features allow for the creation of new agrochemicals with potential applications in pest control, crop protection, and other agricultural areas.
Used in Chemical Research:
Ethyl 4-(3-isopropoxyphenyl)-1,3-diMethylpiperidin-4-yl carbonate is also utilized in chemical research as a model compound for studying the reactivity and properties of ester derivatives of piperidine. Its complex structure provides insights into the behavior of similar compounds and contributes to the advancement of organic chemistry.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 172376-39-5 cis-(+/-)-1,3-dimethyl-4-[3-(1-methyl-ethoxy)phenyl]-4-piperidinol 
• 172376-39-5 C₁₆H₂₅NO₂ 
• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 591-20-8 3-Bromophenol 
• 172376-39-5 cis-(+/-)-1,3-dimethyl-4-<3-(1-methylethoxy)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.

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.

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.

Identification of (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1- piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3- isoquinolinecarboxamide as a novel potent and selective opioid κ receptor antagonist

(3R)-7-Hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1- piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3- isoquinolinecarboxamide (JDTic) was identified as a potent and selective κ opioid receptor antagonist. Structure-activity relationship (SAR) studies on JDTic analogues revealed that the 3R,4R stereochemistry of the 3,4-dimethyl-4-(3-hydroxy-phenyl)piperidine core structure, the 3R attachment of the 7-hydroxy-1,2,3,4-tetrahydroisoquinoline group, and the 1S configuration of the 2-methylpropyl (isopropyl) group were all important to its κ potency and selectivity. The results suggest that, like other κ opioid antagonists such as nor-BNI and GNTI, JDTic requires a second basic amino group to express potent and selective κ antagonist activity in the [35S] GTPγS functional assay. However, unlike previously reported κ antagonists, JDTic also requires a second phenol group in rigid proximity to this second basic amino group. The potent and selective κ antagonist properties of JDTic can be rationalized using the "message-address" concept wherein the (3R,4R)-3,4-dimethyl-4-(hydroxyphenyl)piperidinyl group represents the message, and the basic amino and phenol group in the N substituent constitutes the address. It is interesting to note the structural commonality (an amino and phenol groups) in both the message and address components of JDTic. The unique structural features of JDTic will make this compound highly useful in further characterization of the κ receptor.

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.