Preparation of cisapride

Details Preparation of cisapride Preparation of cisapride

C - Chemistry, Metallurgy

07

D

C07D 211/58 (2006.01) C07D 211/74 (2006.01)

Patent

CA 2176971

Cisapride, i.e. cis-4-amino-5-chloro-N- [1- [3- (4 fluoro-phenoxy)propyl] -3-methoxy-4-piperidinyl] -2-methoxy- benzamide, and similar benzamide derivatives, are prepared from novel 1-aryloxyalkyl- or 1-aralkyl-3-arylcarbonyloxy-4- oxo-piperidines, by nuclear substituent re arrangement involving acyl transfer under animal forming conditions, to give the corresponding 1-aryloxyalkyl- or 1-aralkyl-3-hydroxy- 4-lower alkoxy-4-arylamido piperidine. This in turn is readily converted to the corresponding 3-oxo-4-arylamido- piperidine by reaction with strong organic acid, which can then be reduced, deprotected and 3-methylated to give the final compound, e.g. cisapride.

La présente invention concerne la préparation du cisapride, c'est-à-dire le cis-4-amino-5-chloro-N-[1- [3-(4-fluoro-phénoxy)propyl]-3-méthoxy-4-pipéridinyl]-2-méthoxy-benzamide, et les dérivés benzamides similaires à partir de nouvelles 1-aryloxyalkyl- ou 1-aralkyl-3-arylcarbonyloxy-4-oxo-pipéridines. Le procédé consiste en un réagencement de substituants nucléaires par transfert acyle dans les conditions animales de formation, produisant la 1-aryloxyalkyl- ou 1-aralkyl-3-hydroxy-4-alcoxy(inférieur)-4-arylamido pipéridine correspondante. Celle-ci subit à son tour une conversion donnant, par réaction avec un acide organique fort, la 3-oxo-4-arylamido-pipéridine correspondante, qui peut alors être réduite, déprotégée et 3-méthylatée pour donner le composé final, en l'occurrence le cisapride.

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