Pyridine → HCID 20525731, compound

Participants

Reaction Steps

A slurry of 8.0 g. of 4-(hexadecylamino)phenylacetic acid hydrochloride in 175 ml. of methylene chloride and 50 ml. of glyme containing 10 ml. of thionyl chloride is heated at reflux for 2 hours. The clear solution is concentrated in vacuo giving 9.5 g. of an amber oil. This oil is dilutd with 50 ml. of pyridine containing 0.1 g. of 4-dimethylaminopyridine and 9.1 g. of 3-amino-1,2-propanediol. The reaction is stirred for two days at room temperature. The solution is partitioned between ether and water. The water phase is extracted twice more with 100 ml. of chloroform and ether. The combined organic layer is extracted with water, dried over magnesium sulfate and evaporated to a tacky solid. The solid is recrystallized from acetone-water and then from benzene.

Provenance & Evidence