Water → 3-Butyryl-4-(2-methylphenylamino)-8-(3-piperidinopropoxy)quinoline

Participants

Reaction Steps

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.2 g, 10 mmol) and potassium t-butoxide (5.0 g, 40 mmol) were dissolved in dry dimethylformamide (100 ml) at 80° , then 1-(3-chloropropyl)piperidine hydrochloride (4.0 g, 20 mmol) added and stirred for I hour. The mixture was poured into water, extracted with ether, and the extracts dried and evaporated. Chromatography (silica gel, 3-5% methanolic ammonia in dichloromethane) and recrystallisation from ether/petroleum ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-piperidinopropoxy)quinoline (1.2 g, 27%), m.p. 76°-78°.

Provenance & Evidence