116817-77-7

Basic information

• Product Name: (+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride
• Synonyms: LY-248686(free base); LY-264453; Ariclaim; Yentreve; Cymbalta
• CAS NO: 116817-77-7
• Molecular Formula: C₂H₂O₄*C₁₈H₁₉NOS
• Molecular Weight: 333.8832
• Mol File: 116817-77-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride(116817-77-7)
• EPA Substance Registry System: (+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride(116817-77-7)

Safety Data

• Hazardous Substances Data: 116817-77-7(Hazardous Substances Data)

Usage

General Description

(+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride is a chemical compound with the molecular formula C22H24N2S.HCl. It is a selective serotonin and norepinephrine reuptake inhibitor (SNRI) that is used as an antidepressant medication. (+)-(S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride works by increasing the levels of serotonin and norepinephrine in the brain, which helps to alleviate symptoms of depression and anxiety. The hydrochloride salt form of this compound improves its solubility and stability, making it suitable for use as a pharmaceutical ingredient. As a medication, it is typically taken orally in the form of capsules or tablets, and it has demonstrated effectiveness in the treatment of major depressive disorder and other mood disorders.

Upstream product

• 144-62-7 oxalic acid 
• 116539-58-3 Duloxetine 
• 321-38-0 1-Fluoronaphthalene 
• 896446-94-9 duloxetine ethyl carbamate 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 132335-44-5 (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol 
• 1035456-55-3 C₈H₁₃NO₂S 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 

Downstream Products

• 136434-34-9 duloxetine hydrochloride 
• 116539-58-3 Duloxetine 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF DULOXETINE HYDROCHLORIDE

The present disclosure provides solution to the problem associated in the preparation of duloxetine hydrochloride. This disclosure is successful in preventing the racemization and thereby prevents the formation of unwanted isomer of duloxetine hydrochloride. In addition, the disclosure provides a simple technique for removal of unreacted reactant, 1-fluoronapthalene used as a reactant in the process to obtain (S)-(+)-N-methyl-3(1-naphthalenyloxy)-3-(2-thienyl)propanamine hydrochloride, compound of formula (VI).

Process for making duloxetine and related compounds

A compound of formula 10 is useful in making duloxetine.

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).