116817-12-0

Basic information

• Product Name: S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE
• Synonyms: (S)-N,N-DIMETHYL-3-(NAPHTHALEN-1-YLOXY)-3-(THIOPHEN-2-YL)PROPAN-1-AMINE;S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE;N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate
• CAS NO: 116817-12-0
• Molecular Formula: C19H21NOS·C2H2O4
• Molecular Weight: 401.48
• Mol File: 116817-12-0.mol

Chemical Properties

• Boiling Point: 459.744°C at 760 mmHg
• Flash Point: 231.845°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE(116817-12-0)
• EPA Substance Registry System: S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE(116817-12-0)

Safety Data

• Hazardous Substances Data: 116817-12-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE is used as a pharmaceutical intermediate for the synthesis of various drugs, leveraging its unique structural features to contribute to the development of new therapeutic agents.
Used in Psychiatric and Neurological Applications:
In the field of psychiatry and neurology, S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE is being studied for its potential use in the treatment of disorders, given its interaction with the central nervous system and possible neuromodulatory effects.
Used in Anti-inflammatory and Anti-cancer Applications:
S-(+)-N,N-DIMETHYL-3-(1-NAPHTHLENYLOXY)-3-(2-THIENYL)-PROPANAMINE is also being explored for its anti-inflammatory and anti-cancer properties, indicating its potential role in the development of medications targeting inflammation-related conditions and cancer treatment.

InChI:InChI=1/C19H21NOS/c1-20(2)13-12-18(19-11-6-14-22-19)21-17-10-5-8-15-7-3-4-9-16(15)17/h3-11,14,18H,12-13H2,1-2H3/t18-/m0/s1

Upstream product

• 13636-02-7 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol 
• 321-38-0 1-Fluoronaphthalene 
• 144-62-7 oxalic acid 
• 132335-44-5 (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol 
• 878757-08-5 (R)-(-)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propylamine 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 116817-11-9 N,N-dimethylamino-3-(1-naphthanyloxy)-3-(2-thienyl)-1-propanamine 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 88-15-3 2-Acetylthiophene 

Downstream Products

• 947686-09-1 (S)-N-methyl-N-phenoxycarbonyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propylamine 
• 878757-08-5 (R)-(-)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propylamine 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 116817-11-9 N,N-dimethylamino-3-(1-naphthanyloxy)-3-(2-thienyl)-1-propanamine 

Relevant articles and documents

MANUFACTURING METHOD OF DULOXETINE HYDROCHLORIDE AND DULOXETINE HYDROCHLORIDE WITH NOVEL CRYSTAL STRUCTURE

PROBLEM TO BE SOLVED: To provide a method of providing crystal of (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (general name:duloxetine hydrochloride) useful as an antidepressant with high purity and high bulk density. SOLUTION: There is provided a manufacturing method of duloxetine hydrochloride for depositing the duloxetine hydrochloride in a resulting mixture by mixing a solution by dissolving duloxetine hydrochloride into a solvent for dissolution containing at least one kind of polar solvent selected from water and alcohol having 1 to 3 carbon atoms with acetone, and setting a temperature when dissolving the duloxetine hydrochloride into the solvent for dissolution at 60°C or less. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT

IMPROVED PROCESS FOR THE PREPARATION OF DULOXETINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALT

The present invention relates to an improved process for racemizing one of the enantiomers, or an enantiomerically enriched mixture, of an optically active compound (S)-N, N-dimethyl-3-(2-thienyl)-3-hydroxypropanamine, a key intermediate used for the preparation of (S)-N-methyl-3-(1-naphthalenyloxy)-3-(2- thienyl) propanamine (duloxetine) or its hydrochloride salt. Moreover, the present invention also relates to an improved process for the preparation of (S)-N-methyl-3- (1-naphthalenyloxy)-3-(2-thienyl) propanamine (duloxetine) or its hydrochloride salt having low content of undesired R-isomer and chiral purity not less than 99%.

METHOD FOR THE PREPARATION OF DULOXETINE HYDROCHLORIDE

The present invention relates to an improved process for the preparation of Duloxetine and its intermediates (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine by reacting (S)-(+)-N,N-dimethyl-3-(2-thienyl)-3-hydroxypropanamine with 1-fluoronaphthalene in the presence of a base; wherein the improvement lies in conducting the reaction in the absence of solvent.

AN IMPROVED PROCESS FOR THE PREPARATION OF DULOXETINE AND SALTS THEREOF

The present invention relates to improved process for the preparation of Duloxetine of formula (I) and salts thereof wherein said improvement takes place in step of condensation.

Gastro-resistant pharmaceutical oral compositions comprising duloxetine or its pharmaceutically acceptable derivatives

The present invention relates to a pharmaceutical composition comprising an active core comprising duloxetine or its pharmaceutically acceptable derivatives, a separating layer comprising a water soluble alkaline substance and a gastro-resistant coating comprising a gastro-resistant polymer selected from methacrylic acid copolymers and optionally an over-coating layer.

An investigation on key parameters that influence the synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propylamine: A key intermediate for duloxetine

This document highlights the systematic study of influencing factors such as temperature, base, catalyst, and solvent volume in the synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propylamine oxalate 11a, without affecting the chiral

A METHOD FOR THE PREPARATION OF DULOXETINE HYDROCHLORIDE

The present invention relates to an improved process for the preparation of Duloxetine and its intermediates (S)-(+)-N,N-dimethyl-3-(l-naphthalenyloxy)-3-(2- thienyl)propanamine by reacting (S)-(-)-N,N-dimethyl-3-(2-thienyl)-3-. hydroxypropanamine with 1-fluoronaphthalene in the presence of a base; wherein the improvement lies in conducting the reaction in the absence of solvent.

SYNTHESIS AND PREPARATIONS OF DULOXETINE SALTS

The invention relates to an improved process for the preparation of duloxetine hydrochloride.

Process for the Preparation of 1-Naphthol Mixed Ethers and Intermediates of Crystalline Forms of (+) and (-)-Duloxetine

The invention relates to a process for the preparation of duloxetine (1a), comprising the reaction between 1-fluoronaphthalene and 3-N,N-dimethylamino-1-(2-thienyl)-propan-1-ol in the presence of 1,3-dimethyl-2-oxo-hexahydropyrimidine (DMPU) as the solvent; a method for the identification of duloxetine enantiomers and for the determination of its optical purity is also disclosed.

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).