Potassium Iodide → 4-[Bis(4-fluorophenyl)hydroxymethyl]-N-phenyl-1-piperidinepropanamide

Participants

Reaction Steps

A mixture of 2.0 g (0.007 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 2.6 g (0.014 mole) of 3-chloro-N-phenylpropanamide, 8.5 g (0.080 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath for 16 hours. The mixture was poured into 500 ml of water and extracted twice with 250 ml portions of ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an off-white solid. The solid was recrystallized from methanol/2-propanol to yield 1.9 g (59%) of white solid, mp 190°-192° C.

Provenance & Evidence