Octanoyl chloride → (R)-N-Octanoyl-1-phenylethylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 50.0 g (412.6 mmol) of (R)-1-phenylethylamine and 41.75 g (412.6 mmol) of triethylamine in 750 ml of toluene was cooled to 0° C., and 73.85 g (453.9 mmol) of octanoyl chloride was added dropwise thereto. After completion of the addition, the reaction was allowed to proceed at room temperature for 3 hours. The reaction mixture was again cooled to 0° C. and then the reaction was terminated by addition of 200 ml of 10% hydrochloric acid. The toluene phase was separated, washed with 300 ml of a 10% aqueous solution of sodium hydroxide, and dried over anhydrous sodium sulfate. The solvent was then distilled off, and the residue was quantitated by HPLC. Thus was obtained 19.81 g (97%) of the title compound.

Provenance & Evidence