Methane → HCID 67239030, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-iodoaniline (750 mg, 3.16 mmol) was added to a suspension of 2-pyridyl-piperazine (568 mg, 3.48 mmol), 8-hydroxyquinoline (68 mg, 0.47 mmol) and potassium carbonate (660 mg, 4.74 mmol) in dimethylsulfoxide (5 mL) under an inert atmosphere. Cuprous iodide (94 mg, 0.47 mmol) was added and the reaction mixture was heated at 140-145° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature and poured into a mixture of ammonium hydroxide, ethyl acetate and charcoal and stirred for 30 min. The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulphate and concentrated to dryness in vacuo. The crude product was purified by column chromatography with silica gel (100-200 mesh) using 13% ethyl acetate in petroleum ether as eluent to afford 2-fluoro-4-[4-(2-pyridyl)piperazin-1-yl]aniline (220 mg, 26%) as an orange semi-solid.

Provenance & Evidence