145678-87-1

Basic information

• Product Name: trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine
• Synonyms: (+)-(3R,4S)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE;(+)-(3s,4s)-3,4-diMethyl-4-(3-hydroxyphenyl)piperidine;(-)-3-[(3S,4S)-3,4-Dimethylpiperidin-4-yl]phenol
• CAS NO: 145678-87-1
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Mol File: 145678-87-1.mol

Chemical Properties

• Boiling Point: 335.464 °C at 760 mmHg
• Flash Point: 115.716 °C
• Appearance: /
• Density: 1.009 g/cm³
• CAS DataBase Reference: trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine(145678-87-1)
• EPA Substance Registry System: trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine(145678-87-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 145678-87-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(3R,4S)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Opioid Drug Preparation:
(+)-(3R,4S)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE is used as a crucial component in the preparation of opioid drugs, such as Alvimopan. Its incorporation into the drug's structure contributes to the drug's efficacy and pharmacological properties, making it an essential part of the drug's synthesis process.

Upstream product

• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 444904-02-3 (S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine 
• 223424-24-6 (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine 
• 149541-62-8 Carbonic acid ethyl ester (3R,4S)-4-(3-isopropoxy-phenyl)-1,3-dimethyl-piperidin-4-yl ester 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 149541-62-8 C₁₉H₂₉NO₄ 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 149541-62-8 cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 

Downstream Products

• 441003-83-4 3-[1-(2S-amino-3-methylbutyl)-3S,4S-dimethyl-4-piperidinyl]phenol 
• 361444-66-8 (3R)-7-hydroxy-N-((1S)-1-{[(3S,4S)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide 
• 441003-84-5 (R)-7-Hydroxy-3-{(S)-1-[(3S,4S)-4-(3-hydroxy-phenyl)-3,4-dimethyl-piperidin-1-ylmethyl]-2-methyl-propylcarbamoyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 156130-44-8 2‐((S)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 
• 156130-44-8 2‐((R)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 
• 120938-72-9 LY 255265 
• 120938-72-9 LY 255609 

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.

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.

1,3,4-Trisubstituted-4-arylpiperidines and their preparation

Novel 1,3,4-trisubstituted-4-arylpiperidines are prepared by alkylating a 2,3-disubstituted-3-arylpyrroline to afford a 1,2,3-trisubstituted-3-aryl-1-pyrrolinium salt, reacting the salt with diazomethane to provide a 1,2,3-trisubstituted-3-aryl-1,2-methyl