Hydrochloric Acid → (R)-N-Allyl-N-octanoyl-1-phenylethylamine

Participants

Reaction Steps

A solution of 10.0 g (40.0 mmol) of (R)-N-octanoyl-1-phenylethylamine in 20 ml of toluene, and 9.90 g (80.0 mmol) of allyl bromide were added to a suspension of 3.20 g (80.0 mmol) of sodium hydride (60%) in 74 ml of toluene, and the reaction was allowed to proceed at 100° C. for 6 hours. The reaction mixture was cooled to room temperature and added dropwise to 80 ml of ice-cooled 1 N hydrochloric acid to thereby terminate the reaction. The resulting mixture was extracted with three 30-ml portions of hexane. The organic phase was washed with 50 ml of water and then dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was quantitated by HPLC. Thus was obtained 9.87 g (86%) of the title compound.

Provenance & Evidence