Cheng Yan-xiang
2008
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Journal
Fine and Specialty Chemicals
Abstract
3-(Dimethylamino)propane-1,2-dicarbamate,cationic lipid precursor,was prepared by the reaction of 3-dimethylamino-1,2-propanediol with long-chain alkyl isocyanate,obtained from the reaction based on long-chain alkyl amines and BTC.Factors influencing on the reaction were studied and the following optimum conditions were determined.Using anhydrous toluene as solvent,alkyl isocyanate was prepared with molar ratio of n(BTC):n(alkyl amine)=4:5,at 100℃, then distillation was carried out under reduced pressure,the yield was 87%.Afterward the following procedures were carried out to prepare 3-(dimethylamino)propane-1,2-dicarbamate, reacting alkyl isocyanate with 3-dimethylamino-1,2-propanediol in 2.1:1 of molar ratio in the presence of triethylamine as catalyst and anhydrous toluene as solvent,refluxing for 12 hours, purifying then by column chromatography,after the solvent was distilled off,the yield was 45%. The structure of product was confirmed by ~1H NMR,~(13)C NMR,IR and HRMS.