Potassium Hydroxide → cis-5-amino-4-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide

Participants

Reaction Steps

A mixture of 81 parts of ethyl cis-4-[(5-amino-4-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinecarboxylate, 122 parts of potassium hydroxide and 800 parts of 2-propanol was stirred for 6 hours at reflux temperature. The whole was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was taken up in water and heated for a while. The mixture was evaporated again. The residue was taken up in water and the aqueous phase was extracted twice with dichloromethane. The combined organic layers were washed with water, dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 58 parts (85%) of cis-5-amino-4-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide; mp. 191.8° C. (interm. 15).

Provenance & Evidence