Stearamidopropyl Dimethylamine → N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(octadecanoylamino)propyl)ammonium chloride

Participants

Reaction Conditions

Reaction Steps

A 36.86 g (0.100 mol) portion of N-octadecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 100 ml of chloroform were put into a flask, and 23.30 g (0.101 mol) of geranyl chloroacetate was added thereto at 25° C. spending 5 minutes. The reaction mixture was stirred at 25° C. for 36 hours and then, after confirming by 1H-NMR that chloroacetate was mostly disappeared, the solvent was evaporated under a reduced pressure. The thus obtained viscous oil was dissolved in 200 ml of acetone and cooled to 5 to 10° C. to effect precipitation of a white precipitate. The supernatant solvent was discarded, and the precipitated was collected and dried under a reduced pressure to obtain the title compound (to be referred to as betaine ester (1) hereinafter) as a slightly brownish white solid. Yield 49.1 g (0.0819 mol; yield 81.9%).

Provenance & Evidence