Methanol → HCID 178501195, compound

Participants

Reaction Steps

Thionyl chloride (0.65 g, 5.47 mmol) was added to a stirred solution of cis-4-(phenylamino)cyclohexanecarboxylic acid hydrochloride (600 mg, 2.74 mmol) in MeOH (10 ml) at room temperature and heated at reflux for 5 h. The reaction mixture was concentrated under reduced pressure. The crude product was basified with saturated sodium bicarbonate solution and extracted with DCM (2×25 ml). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound which was purified by column chromatography over neutral alumina by eluting in 10% ethyl acetate in petroleum ether to afford 500 mg of cis-methyl 4-(phenylamino)cyclohexanecarboxylate (78%) as colorless oily liquid.

Provenance & Evidence