Sodium hydride → 2-(1-t-Butoxycarbonyl-3-piperidylthio)--3-phenylquinoline

Participants

Reaction Steps

3-Phenylquinolin-2-thione (5.2 g.) was added to a suspension of sodium hydride (1.15 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (35 ml.) at 0°-5°. When all the hydrogen had evolved, 1-t-butoxycarbonyl-3-p-toluenesulphonyloxypiperidine (7.8 g.) was added and the mixture was heated at 80° for 2 hr. The mixture was cooled to ambient temperature poured into ice-water (350 ml.) and extracted with ethyl acetate (3×150 ml). The ethyl acetate extract was washed with brine (150 ml.) and then dried (MgSO4). The solvent was evaporated to give 2-(1-t-butoxycarbonyl-3-piperidylthio)--3-phenylquinoline, which was used without further purification.

Provenance & Evidence