Triethylamine → Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-(t-butoxycarbonyl)piperazine (7 g, 1 mol. equiv.) in dichloromethane (ml) at 0° C. under nitrogen was added triethylamine (6.29 ml, 1.2 mol. equiv.). The mixture was vigorously stirred whilst methanesulphonyl chloride (3.49 ml, 1.2 mol. equiv.) was added, dropwise. The mixture was then stirred for twenty four hours. The reaction mixture was washed with a saturated aqueous sodium bicarbonate solution (30 ml) and the organic layer dried using magnesium sulphate. The organic solvent was removed under reduced pressure and the residue purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (1:2, by volume) to give the title compound (6.93 g). TLC Rf=0.37 (silica, ethyl acetate:hexane, 1:2, by volume). LRMS m/z=282(m+NH4)+. Found: C, 45.25; H, 7.68; N, 10.49. C10H20N2SO4 requires C, 45.43; H, 7.63; N, 10.60%.

Provenance & Evidence