Acetyl chloride → HCID 18967525, compound

Participants

Reaction Steps

A solution of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.238 g, 0.986 mmol) and triethylamine (0.144 mL, 1.08 mmol) in acetonitrile (12 mL) was chilled to 0° C. and acetyl chloride (0.077 mL, 1.08 mmol) was added all at once. The mixture was heated to reflux for 7 hours and cooled to room temperature. (TLC with 40% methanol/ethyl acetate indicated that the reaction was complete.) The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The organic solution was extracted with saturated sodium bicarbonate and brine, then it was dried over calcium sulfate and concentrated to a light tan solid (0.115 g). Trituration with hexane gave 0.09 g (33%) of the title product as a tan solid: mp 173°-177° C. A sample recrystallized from ethyl acetate was submitted for analysis: mp 177°-180° C. HRMS m/e calculated for C17H29N3O: 283.1682. Observed m/e: 283.1678.

Provenance & Evidence