Water → HCID 20542605, compound

Participants

Reaction Steps

A solution of 1-methyl-4-phenyl-4-piperidinol (7.65 g, 40 mM) in DMSO (50 ml) was treated with 50% sodium hydride dispersion (2 g, 40 mM) and warmed to 80° until a homogenous solution was obtained. After cooling to room temperature, the mixture was treated with a solution of 2-chloroquinoline (6.55 g, 40 mM) in DMSO (10 ml). After 24 hours the mixture was poured on to water (250 ml) and extracted with toluene (3×250 ml). After drying and evaporation of the solvents, the residue crystallised from cyclohexane to give recovered 1-methyl-4-phenyl-4-piperidinol (2.7 g). Chromatography of the mother liquors on Grade III silica, using 3% methanol in chloroform as eluant gave the title compound (3 g) contaminated with a small quantity of 2-quinolone which was removed by crystallisation from cyclohexane. Recrystallisation of the mother liquors from pentane gave the title compound (1.2 g) m.p. 80°-1° C.

Provenance & Evidence