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1. (WO1998051685) METHOD OF MANUFACTURING SERTINDOLE

Pub. No.:    WO/1998/051685    International Application No.:    PCT/DK1998/000183
Publication Date: Fri Nov 20 00:59:59 CET 1998 International Filing Date: Fri May 08 01:59:59 CEST 1998
IPC: C07C 227/08
C07C 227/18
C07C 229/58
C07D 401/04
C07D 401/14
Applicants: H. LUNDBECK A/S
BECH SOMMER, Michael
Inventors: BECH SOMMER, Michael
Title: METHOD OF MANUFACTURING SERTINDOLE
Abstract:
A process of manufacturing sertindole comprising preparation of N-(4-fluorophenyl)-N-(2-carboxy-4-chlorophenyl)glycine, by reacting an alkalimetal salt of 2,5-dichlorobenzoic acid with an alkalimetal salt of N-(4-fluorophenyl)glycine in an aqueous, alkaline environment in the presence of a copper catalyst; cyclisation of N-(4-fluorophenyl)-N-(2-carboxy-4-chlorophenyl)glycine to the corresponding 3-acetoxy-indole; reduction of the 3-acetoxy-indole and subsequent elimination of H2O thereby obtaining 5-chloro-1-(4-fluorophenyl)indole which is reacted with 4-piperidone in a mixture of an acetic acid and concentrated HC1; reduction of the resulting 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole and reaction of this compound with 1-(2-chloroethyl)-2-imidazolidinon in order to obtain sertindole. Alternatively, 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole is first reacted with 1-(2-chloroethyl)-2-imidazolidinon followed by reduction thereby obtaining sertindole. This process uses reactants and solvents that are suitable and allowed in large scale manufacture. Furthermore good total yields are obtained.