175591-23-8

Basic information

• Product Name: 3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol
• Synonyms: 3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol;tapentadol;3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol;3-((2R,3R)-1-(DiMethylaMino)-2-Methylpentan-3-yl)phenol;Phenol, 3-[(1R,2R)-3-(diMethylaMino)-1-ethyl-2-Methylpropyl]-
• CAS NO: 175591-23-8
• Molecular Formula: C₁₄H₂₃NO
• Molecular Weight: 221.34
• Mol File: 175591-23-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 323.493 °C at 760 mmHg
• Flash Point: 134.18 °C
• Appearance: /
• Density: 0.97 g/cm³
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.518
• PKA: 9.97±0.10(Predicted)
• CAS DataBase Reference: 3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol(175591-23-8)
• EPA Substance Registry System: 3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol(175591-23-8)

Safety Data

• Hazardous Substances Data: 175591-23-8(Hazardous Substances Data)

Usage

Uses

Analgesic (μ-agonist).

Pharmacology

Tapentadol, a relatively new opioid, also has distinct mechanisms of analgesic action. It is a MOP receptor agonist more potent than tramadol. It also acts by selectively inhibiting reuptake of noradrenaline, and therefore there may be a rationale for using it in patients with pain with neuropathic features.

InChI:InChI=1/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3

Upstream product

• 2972-72-7 2-(3-methoxybenzylidene)malononitrile 
• 591-31-1 3-methoxy-benzaldehyde 
• 515114-52-0 (±)-3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol 
• 175591-22-7 (βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine 
• 24393-44-0 2-cyano-3-(3-methoxyphenyl)acrylic acid ethyl ester 
• 1313429-15-0 2-[1-(3-methoxy-phenyl)-propyl]-malononitrile 
• 1313429-18-3 3-(3-methoxy-phenyl)-2-(toluene-4-sulfonyl)-pentanoic acid ethyl ester 
• 1313429-19-4 3-(3-methoxy-phenyl)-2-(toluene-4-sulfonyl)-pentanenitrile 
• 1313429-21-8 2-[1-(3-methoxy-phenyl)-propyl]-2-methyl-malononitrile 
• 1313429-22-9 3-(3-methoxy-phenyl)-2-methyl-2-(toluene-4-sulfonyl)-pentanoic acid ethyl ester 
• 1313429-23-0 3-(3-methoxy-phenyl)-2-methyl-2-(toluene-4-sulfonyl)-pentanenitrile 
• 1313429-24-1 2-methyl-3-(3-methoxyphenyl)pentanenitrile 
• 1313429-25-2 2-cyano-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid 
• 1616-70-2 2-methyl-3-(3-methoxyphenyl)valeric acid 

Downstream Products

• 175591-09-0 tapentadol hydrochloride 
• 1314003-88-7 (R,R)-tapentadol-(PABA tert-butyl ester) carbamate 
• 1356394-24-5 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol nitrate 
• 1356394-25-6 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol nicotinate 
• 1356394-28-9 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol malonate 
• 1356394-26-7 tapentadol bisulfate 
• 1356475-57-4 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol hydrobromide 
• 1356394-20-1 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol sebacinate 
• 1356394-21-2 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol 1-hydroxy-2-naphthoate 
• 1356394-22-3 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol embonate 
• 1360871-13-1 C₂₃H₃₈N₂O₂ 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF TAPENTADOL AND ANALOGS THEREOF

The present invention relates to a process for the preparation of tapentadol and analogs or compounds or stereoisomers of formula (I), Formula I wherein, A is aryl, heteroaryl, and cycloalkyl; R is H, OH, OR1, halogen, C1-C12 alkyl, cycloalkyl, aryl or heteroaryl; R1 is C1-C12 alkyl, cycloalkyl, aryl or heteroaryl, wherein each of these groups may further be substituted with one or more substituent selected from H, OH, halogen, CN, NO2, C1-C4 alkyl or phenyl. Further, the multi-step process involves no column chromatography purification until the very last step. This makes this process highly commercially viable and industrially useful.

A kind of dual role of analgesic of the center of the new compound, preparation method and use thereof

The invention relates to a central-analgesic novel compound having double effects, or a pharmaceutical salt or a hydrate thereof, a preparation method of the novel compound and an application of the novel compound in drugs. The compound is represented as

PROCESS FOR THE PREPARATION OF 3-[(1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL]-PHENOL

A process for the preparation of a compound of formula (I) and of a acid salt (T) wherein R1 is selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R2 and R3, are, independently of each other, selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R4, R5, R6 and R7, are independently of each other, selected from the group consisting of H, alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, and wherein the acid salt is a 2,3-Ditoluoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid salt, 2,3-Dianisoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid mono(dimethylamide) salt or a mixture of two or more thereof, wherein the tartaric acid salt (T) of the compound of formula (I) contains at least 90 % by weight of the tartaric salt of the compound of formula (Ia) based on the total weight of the acid salt of the compound of formula (I).