Triethylamine → 2-(4-Methylpiperidin-1-yl)ethan-1-ol

Participants

Reaction Steps

A mixture of 4-methylpiperidine (10 g, 0.10 mol), 2-bromoethanol (12.5 g, 0.10 mol), and triethylamine (15 g, 0.15 mol) in CHCl3 (100 mL) was stirred at room temperature for two days. The mixture was concentrated, and the residue was purified on a silica gel column (eluting with NH3—H2O/MeOH/DCM=1/6/300) to give 2-(4-methylpiperidin-1-yl)ethanol (3 g) as a colorless oil. 1H NMR (CDCl3): δ 3.57 (m, 2H), 3.24 (br s, 1H), 2.84 (m, 2H), 2.47 (m, 2H), 2.00 (dt, 2H), 1.58 (m, 2H), 1.35 (m, 1H), 1.21 (dt, 2H), 0.89 (d, 3H); LCMS: 144 (M+H)+.

Provenance & Evidence