Sodium Hydroxide → 1-(Methylsulphonyl)piperidin-4-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-piperidone hydrate hydrochloride (40.00 g, 0.260 mol) and THF (320 ml) was added CH3SO2Cl (31.0 ml, 0.402 mol) and 15% aq. NaOH (156 ml) such that the temperature of the reaction mixture was maintained at 26-32° C. After this addition, the reaction mixture was stirred at RT for 2 hours and transferred to a separatory funnel. The organic layer was collected and the aqueous layer was extracted with THF (2×250 ml). The combined organic layers were dried over Na2SO4. After filtration, the concentrated residue was washed with hexane to give the product (46.0 g, 100%). 1H NMR (CDCl3) δ 3.59 (t, J=6.00 Hz, 4H), 2.89 (s, 15 3H), 2.59 (t, J=5.6 Hz, 4H).

Provenance & Evidence