1313374-09-2

Upstream product

• 15851-92-0 (E)-3-methoxycinnamoyl chloride 
• 1313429-32-1 (αR,βR)-β-ethyl-3-methoxy-α-methylbenzenepropanoic acid 
• 1313429-34-3 (S),(S)-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid 
• 124-40-3 dimethyl amine 
• 1313374-18-3 (Z,E)-3-(3-methoxyphenyl)-N,N,2-trimethylpent-2-enamide 
• 1352230-10-4 3-hydroxy-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamide 
• 1313374-17-2 N,N-dimethyl-2-methyl-3-(3-methoxyphenyl)valeramide 
• 1313429-14-9 2-cyano-3-(3-methoxy-phenyl)-pentanoic acid ethyl ester 
• 1313429-33-2 (R),(R)-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid (R)-(+)-α-methylbenzylamine salt 
• 1313429-27-4 3-(3-methoxy-phenyl)-2-methyl-pentanoic acid ethyl ester 
• 1313429-26-3 diethyl 1-(3-methoxyphenyl)propylmethylmalonate 
• 1616-70-2 2-methyl-3-(3-methoxyphenyl)valeric acid 
• 1313429-25-2 2-cyano-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid 
• 1313429-24-1 2-methyl-3-(3-methoxyphenyl)pentanenitrile 

Downstream Products

• 175591-09-0 tapentadol hydrochloride 
• 175591-23-8 tapentadol 
• 175591-22-7 (βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine 

Relevant academic research and scientific papers

Substituted n-pentanamide compounds, preparation method and the use thereof

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

SUBSTITUTED N-PENTANAMIDE COMPOUNDS, PREPARATION METHODS AND USES THEREOF

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

A NOVEL PROCESS FOR THE PREPARATION OF TAPENTADOL OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Disclosed herein is a novel, commercially viable and industrially advantageous process for the preparation of 3-[(1R,2R))-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol (Tapentadol), or a pharmaceutically acceptable salt thereof, in high yield and purity. Also described are novel intermediates useful for preparing tapentadol or a pharmaceutically acceptable salt thereof.

O-SUBSTITUTED (2R,3R)-3-(3-HYDROXYPHENYL)-2-METHYL-4-PENTENOIC ACIDS AND A METHOD OF OBTAINING THE SAME

The compounds of general formula II are new and represent important intermediates in the synthesis of tapentadol. In the synthesis of tapentadol of formula I and its pharmaceutically acceptable salts, O-protected (2R,3R)-acids of general formula II, in step A, are reacted in an inert organic solvent with an activating agent, optionally in presence of a catalyst or a base; in step B, the obtained compounds of general formula V, wherein R has the above mentioned meaning and X stands for chlorine or alkoxycarbonyloxyl group O-CO-OR1 or pivaloyloxyl O-CO-t-Bu group, wherein R1 is methyl or ethyl, are reacted with dimethylamine or its salts optionally in presence of a base; in step C, the obtained N, N-dimethylamides of general formula VI, wherein R has the above mentioned meaning, are reduced by means of hydride agents in a suitable solvent; in step D, the produced alkeneamines of general formula VII, wherein R has the above mentioned meaning, are hydrogenated on a metal catalysts in a suitable solvent; and, finally, in step E, the produced alkaneamines of general formula VIII, wherein R has the above mentioned meaning, are O-dealkylated by means of dealkylating agents, and, if required, the obtained tapentadol is converted by the action of a pharmaceutically acceptable acid to respective salts, e.g. hydrochloride.

INTERMEDIATE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF TAPENTADOL AND RELATED COMPOUNDS

The present invention discloses processes for the preparation of 3-[(1R,2R)-3-(dimethyl- amino)-1-ethyl-2-methylpropyl]phenol (Tapentadol), salts thereof and related compounds of formula (A), including stereoisomers and pharmaceutically acceptable salts t

Process for Preparing Substituted 3-(1-amino-2-methylpentane-3-yl)phenyl Compounds

A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds.

PROCESS FOR THE PREPARATION OF 1-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVES

A process for the preparation of 1-phenyl-3-dimethylaminopropane derivatives of formula (I) and its pharmaceutically acceptable salts thereof from cyano intermediate of formula (II), wherein R1 can be selected from -OR2, halo, -CH2OR2, -SR2, -SOR2, SO2R2, -SO3H, -NO2, -NR2R2', -CONR2R2', carboxylic esters, sulfonate esters or phosphate esters, R2 and R2' can be same or different, and can be selected from hydrogen, alkyl, aryl, aralkyl, heteroaryl, -COR2", -P03(R2")2 wherein R2" can be selected from alkyl, aryl, aralkyl, heteroaryl and the like.