Sodium Hydroxide → N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide propanoate ethanedioate

Participants

Reaction Steps

A mixture of 8 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinemethanol and 35 parts of propanoic acid anhydride is stirred and refluxed for 3 hours. After cooling, the reaction mixture is poured onto 300 parts of ice-water and the whole is alkalized with sodium hydroxide solution. The product is extracted with 1,1'-oxybisethane. The extract is washed with water, dried, filtered and evaporated. The residue is dissolved in 140 parts of 2,2'-oxybispropane 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-propanone. The salt is filtered off and dried, yielding N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide propanoate ethanedioate; mp. 182° C.

Provenance & Evidence