Formaldehyde → N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

Participants

Reaction Steps

Formaldehyde (166 mg, 5.55 mmol) was added to a solution of O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl) hydroxylamine (200 mg, 0.617 mmol) in 1,2-dichlorethane (5 ml) and stirred at room temperature for 3 hours. Sodium triacetoxyborohydride was added and stirred at room temperature for 12 hours. The reaction mixture was diluted with of ethyl acetate (30 ml), washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (the residue was purified by preparative TLC (ethyl acetate/petroleum ether: 67/33) to give N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (125 mg, 60%) as a white solid.

Provenance & Evidence