Sodium hydride → HCID 20306014, compound

Participants

Reaction Steps

N-Acetyl-4-hydroxypiperidine (13.6 g.) in dimethylformamide (50 ml.) was added dropwise to a stirred suspension of sodium hydride (10 g. 50% dispersion in mineral oil) in dimethylformamide (50 ml.) under nitrogen. The mixture was stirred at room temperature for 3 hours then α-(bromomethyl)styrene (20 g.) in dimethylformamide (50 ml.) was added dropwise. The mixture was stirred at room temperature for 4 hours, then diluted with water and extracted with chloroform (3×200 ml.). The combined chloroform extracts were dried (Na2SO4), evaporated in vacuo, and distilled to give N-acetyl-4-(2-phenylallyloxy)piperidine (25 g.), b.p. 170°-180° C./0.3 mm. with an n.m.r. spectrum in accordance with this structure.

Provenance & Evidence