Ammonium Hydroxide → N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.8 parts of 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]ethanone and 15 parts of propanoic acid, anhydride is stirred for 5 hours at 180° C (oil-bath). Stirring is continued overnight, while meantime the mixture is allowed to reach room temperature. The reaction mixture is poured onto ice-water and the whole is alkalized with a concentrated ammonium hydroxide solution. The product is extracted with benzene. The extract is washed twice with water, dried, filtered and evaporated in vacuo. The residue is dissolved in 1,1'-oxybisethane and the solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from 2-propanol, yielding N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide ethanedioate; mp. 196.8° C.

Provenance & Evidence