Benzyl Alcohol → HCID 20525847, compound

Reaction equation

Cl.[CH2:2]([NH:18][C:19]1[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][C:25](Cl)=[O:26])=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH2:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:2]([NH:18][C:19]1[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][C:25]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:26])=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Procedure

A sample of 10.0 g. of 4-(hexadecylamino)hydrocinnamoyl chloride hydrochloride is treated with 9.5 g. of 4-dimethylaminopyridine and 2.5 g. of benzyl alcohol in 80 ml. of methylene chloride and the solution is heated to reflux for 4 hours. The reaction solution is then cooled, washed twice with water and dried over magnesium sulfate. The methylene chloride solution is passed through a pad of alumina. The filtrate is concentrated and the residue recrystallized from chloroform-hexane to yield benzyl 4-(hexadecylamino)hydrocinnamate.