Methanol → N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amine

Participants

Reaction Steps

Into a cooled solution of 5.0 g (9 mmol) of N-allyl-N,N-dioctadecylamine in 50 ml of methylene chloride at 0° C. under a nitrogen atmosphere is added dropwise with stirring a solution of 1.54 g (9 mmol) of 85% active m-chloroperbenzoic acid in 50 ml of methylene chloride. After the addition is complete (approximately 15 minutes), the resultant solution is allowed to warm to ambient temperature (about 22°-24° C.). The reaction is complete after about 5 hours when TLC analysis (silica gel, 19:1 v/v ethyl acetate:methanol)indicates the starting material has completely reacted. The reaction mixture is transferred to a separatory funnel and washed sequentially with three 50 ml portions of 10% aqueous sodium hydroxide solution and then with 100 ml of distilled water. The organic layer is dried over anhydrous sodium sulfate and heated under reflux at approximately 40° C. for two hours. The resultant solution is concentrated in vacuo and the residue is purified by flash chromatography (silica gel, 94:6 v/v hexane:ethyl acetate eluent) to give 3.3 g (64% yield) of the title compound as a white solid melting at 62°-65° C.

Provenance & Evidence