Piperidine → HCID 16722802, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-fluoro-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (200 mg, 0.62 mmol) in DMSO (2 mL) was added piperidine (307 μL, 3.11 mmol) and the resulting mixture stirred for 5 h at 170° C. After cooling to ambient temperature the reaction mixture was extracted with aqueous hydrochloric acid (1 N, 20 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL) and the combined organic layers were washed with brine (half-saturated, 20 mL) and aqueous sodium carbonate (saturated, 20 mL). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=80:0:20 to 50:30:20) afforded the title compound (192 mg, 80%) as a white solid. MS: m/e=387.1 [M+H]+.

Provenance & Evidence