Hydrochloric Acid → (2R*,4S*)-2-(4-Chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-(4-quinolinylmethyl)-4-piperidinamine

Participants

Reaction Steps

A mixture of 550 mg (1.54 mmol) of (2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-4-piperidinamine and 242 mg (1.54 mmol) of 4-quinolinecarboxaldehyde are dissolved in 30 ml of toluene and evaporated to dryness under reduced pressure. This is repeated twice more. The residue is taken up in 10 ml of ethanol, 70 mg (1.85 mmol) of sodium boranate are added and the mixture is stirred at 25° for 3 hours. It is acidified with 1N hydrochloric acid and left to stir for 1 hour. The reaction mixture is poured into saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude product is recrystallised twice from ethyl acetate and yields 320 mg of the title compound of the formula ##STR110## in the form of white crystals; melting point 148°-9°; MS: M+497.

Provenance & Evidence