Epichlorohydrin → n-[1-(4-Chlorophenyl)-1-methylethyl]-2,3-epoxypropylamine

Reaction equation

[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH2:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH:16][CH2:1][CH:3]2[O:5][CH2:4]2)([CH3:14])[CH3:15])=[CH:11][CH:12]=1

Participants

Procedure

Epichlorohydrin (8.05 ml) was added dropwise to a solution of 1-(4-chlorophenyl)-1-methylethylamine (17.38 g) in methanol (17.5 ml) at 0° C. with stirring. The solution was warmed to ambient temperature and stirred for 48 hours. Sodium hydroxide solution (50%) (17.5 ml) was added and the mixture stirred for 15 minutes. The product was extracted with ether to give an oil which was purified by flash column chromatography on silica using petroleum ether, b.p. 40-60° C./ethyl acetate/triethylamine (8:2:1) as the mobile phase with gradually increasing amounts of ethyl acetate to give N-[1-(4-chlorophenyl)-1-methylethyl]-2,3-epoxypropylamine as an oil.