Sodium Hydroxide → 4-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

Participants

Reaction Steps

To a stirred and gently refluxing solution of 43 parts of ethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate in 288 parts of dry benzene is added dropwise a solution of 33.9 parts of sodium dihydro-bis(2-methoxyethoxy)aluminate 70% in 72 parts of dry benzene without heating. Upon completion, stirring is continued for 3 hours at reflux. The reaction mixture is allowed to cool to room temperature overnight and poured onto 1000 parts of ice-water. The resulting emulsion is decomposed by the addition of a concentrated sodium hydroxide solution. The organic layer is separated and filtered over hyflo. The filter-cake is washed thoroughly with benzene. The filtrate is dried, filtered and evaporated. The residue is crystallized from 385 parts of 2,2'-oxybispropane. The crude solid product is filtered off and recrystallized from 2-propanol, yielding 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinemethanol; mp. 96.7° C.

Provenance & Evidence