Triethylamine → tert-Butyl 4-[(methanesulfonyl)amino]piperidine-1-carboxylate

Participants

Reaction Steps

tert-Butyl 4-aminopiperidine-1-carboxylate (0.10 g, 0.50 mol) was combined with methanesulfonyl chloride (0.043 mL, 0.56 mol) and triethylamine (0.21 mL, 1.5 mmol) in methylene chloride (2 mL) at room temperature and stirred for 2 hours. The reaction was diluted with dichloromethane, washed with water, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give tert-butyl 4-[(methylsulfonyl)amino]piperidine-1-carboxylate, LCMS [M+Na]+: m/z=301.0. The later was treated with 4.57 M hydrogen chloride in 1,4-dioxane (1 mL, 4 mmol) at room temperature for 1 hour. The mixture was concentrated to give the desired HCl salt, which was used directly in the next step. LCMS calculated for C6H15N2O2S (M+H)+: m/z=179.1; Found: 179.1.

Provenance & Evidence