C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 401/14 (2006.01) C07D 401/04 (2006.01)
Patent
CA 2486883
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 HCI; 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.
H. Lundbeck A/s
Robic
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