1056204-99-9

Basic information

• Product Name: (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-benzoyl-(L)-tartrate
• Synonyms: (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-benzoyl-(L)-tartrate
• CAS NO: 1056204-99-9
• Molecular Weight: 669.752
• Mol File: 1056204-99-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-benzoyl-(L)-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-benzoyl-(L)-tartrate(1056204-99-9)
• EPA Substance Registry System: (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-benzoyl-(L)-tartrate(1056204-99-9)

Safety Data

• Hazardous Substances Data: 1056204-99-9(Hazardous Substances Data)

Upstream product

• 2743-38-6 O,O'-dibenzoyl-L-tartaric acid 
• 116817-11-9 N,N-dimethylamino-3-(1-naphthanyloxy)-3-(2-thienyl)-1-propanamine 

Downstream Products

• 132335-46-7 N-methyl-(S)-duloxetine 

Relevant articles and documents

NOVEL PROCESS FOR PREPARATION OF DULOXETINE HYDROCHLORIDE

An improved, safer and easy to operate on plant scale process for synthesis of duloxetine hydrochloride (1) having chiral purity greater than 99.9% that is characterized by the following: (i) preparation of racemic condensed compound (RS)-N,N-di methyl-3- (1-naphthyloxy)-3-(2-thienyl)propanamine (4) by reaction of racemic hydroxy compound (2) with 1-fluronaphthalene (3) in presence of a base such as sodamide, potassium amide or potassium bis(trimethylsilyl)amide (KHDMS) in polar aprotic solvent, (ii) optical resolution of racemic condensed compound (5a + 5b) with di-benzoyl-L-tartaric acid (7, DBTA, R = H) or di-para-anisoyl-L-tartaric acid (7, DATA, R = OCH3) to obtain crude (S)-N.N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine dibenzoyl tartarate salt (8a) or (S)-N.N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine di-p-anisoyl tartarate salt (9a) respectively, (iii) optionally purification of crude tartarate salts (8a or 9a) by crystallization, (iv) optionally purification of duloxetine hydrochloride (1) by crystallization and (v) racemization of undesired (R)-N,N-di methyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine (5b) by treatment with base potassium bis(trimethylsilyl)amide (KHDMS) to obtain racemic mixture of condensed compounds (5a and 5b). A novel salt S(+)-N.N-dimethyl-3-(1-naphthylenyloxy)-3-(2-thienyl)propanamine dibenzoyl -(L)- tartarate (8a) and S(+)-N.N-dimethyl-3-(1-naphthylenyloxy)-3-(2-thienyl)propanamine di-p-anisoyl-(L)- tartarate (9a). Novel process for racemization of undesired (R)-N,N-di methyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine (5b) by treatment with KHDMS to obtain racemic mixture condensed compounds (5a and 5b).