Preparation of cisapride
AssigneeTorcan Chemical Ltd.
InventorsYee-Fung Lu, Raymond So, Clarke Slemon, Jan Oudenes, Teng-Ko Ngooi
Life of this patent
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Abstract
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.
Claims7
1-Aryloxyalkyl- or 1-aralkyl-3-hydroxy-4-loweralkoxy-4-arylamido piperidines of the general formula B:
- ##STR8## in which L represents aralkyl or aryloxyalkyl in which the alkyl portion has from 1 to 6 carbon atoms and the aryl nucleus is optionally substituted with up to 3 substituents independently selected from halo, lower alkyl and lower alkoxy, or alkyl having from 1 to 6 carbon atoms;
- R represents a phenyl group optionally substituted with up to three substituents independently selected from halo, amino, protected amino, alkyl of from 1 to 6 carbon atoms, and alkoxy of from 1 to 6 carbon atoms;
- and R' represents alkyl of 1-6 carbon atoms, or benzyl.
Dependencies are inferred from the claim text.