Allyl bromide → N-acetyl-4-allyloxypiperidine

Participants

Reaction Steps

A solution of N-acetyl-4-hydroxypiperidine (100 g) in dimethylformamide (250 ml) was added dropwise to sodium hydride (38 g, 50% mineral oil dispersion) under an atomsphere of nitrogen. The mixture was stirred for 2 hours then allyl bromide (93 g) was added slowly while maintaining the reaction temperature at 25° by external cooling. The mixture was then stirred at room temperature overnight, diluted with isopropanol (20 ml) and ether (500 ml), filtered, and evaporated in vacuo. Distillation of the residue gave N-acetyl-4-allyloxypiperidine (108.8 g), b.p. 128°/2 mm, identified spectroscopically.

Provenance & Evidence