Chloroform → 2-Chloro-N-(2-chloroethyl)-N-(2-phenylethyl)ethan-1-amine--hydrogen chloride (1/1)
Reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:13]CO)[CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O.[CH:20]([Cl:23])(Cl)Cl>>[ClH:18].[C:1]1([CH2:7][CH2:8][N:9]([CH2:13][CH2:20][Cl:23])[CH2:10][CH2:11][Cl:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Procedure
To a solution of 20.0 g (95 mmoles) of N-(2-phenylethyldiethanolamine in 40 mL of chloroform was added, over a period of 1 hour, 20 mL of thionyl chloride in 20 mL of chloroform. The mixture was heated under reflux for 2 hours and concentrated to give N-(2-phenylethyl)-N,N-bis(2-chloroethyl)amine hydrochloride as an oil. NMR (CDCl3) δ7.2-7.4 (m, 5H); 4.1 (t, 4H); 3.6 (t, 4H); 3.5 (m, 2H) and 3.2 (m, 2H).