Acetic Acid → HCID 66799229, compound

Participants

Reaction Steps

Acetic acid (0.2 ml) was added catalytically to an ice-cooled (0° C.) solution of 4-(pyridin-4-yl)cyclohexanone (500 mg, 2.857 mmol, 1 eq) and methylamine hydrochloride (957 mg, 14.28 mmol, 5 eq) in MeOH (10 ml), and stirring was carried out for 1 h at RT. NaCNBH3 (358 mg, 5.714 mmol, 2 eq) was added at 0° C. and stirring was carried out for a further 14 h at RT. The reaction mixture was concentrated, diluted with dichloromethane (100 ml) and washed with sat. sodium hydrogen carbonate solution (60 ml) and sat. NaCl solution (60 ml). The organic phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (Alox neutral, 6% MeOH in dichloromethane). The desired amine was obtained in the form of a light-yellow solid. Yield: 27% (150 mg, 1.26 mmol).

Provenance & Evidence