2-Methylpiperidine → 2-Methyl-1-(2-propynyl)piperidine

Participants

Reaction Steps

A flask was charged with propargyl chloride (17.27 g, 0.232 mol, 70 wt % in toluene) in dry methanol (21 mL) under nitrogen atmosphere. (+/−)-2-Methyl-piperidine (55 mL, 0.46 mol) in dry methanol (43 mL) was added via drop-wise addition over 30 minutes. The material was stirred overnight. The mixture was placed on a rotovap and about half the volume of methanol was stripped, providing a precipitate. The solid precipitate was removed by filtration, rinsing through with ether (150 mL). The filtrite was placed on the rotovap and concentrated. Another small amount of precipitate was removed by filtration. The remaining oily product was purified by distillation providing 7.23 g (bp=180-185° C.) of (+/−)-2-methyl-1-prop-2-ynyl-piperidine as a clear mobile oil.

Provenance & Evidence