Chloroform → N,N-dibenzyl-1-(oxiran-2-yl)methanamine

Reaction equation

Cl[CH2:2][CH:3]([OH:20])[CH2:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].C(Cl)(Cl)Cl>O>[CH2:6]([N:5]([CH2:4][CH:3]1[CH2:2][O:20]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Procedure

50.7 g (0.175 mol) of 1-chloro-3-dibenzylamino-2-propanol, 9.5 g (0.24 mol) of sodium hydroxide and 5 ml of water are stirred together for 1 hour at 95° C. After the addition of 50 ml of chloroform and 20 ml of water, the phases are separated and the organic phase is washed with 20 ml of water, dehydrated with sodium sulphate and concentrated by evaporation. Vacuum distillation of the yellow oil obtained yields 33.7 g (76%) of the oxirane as a colourless oil.