3,4-Dichlorobenzyl chloride → 3-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-ol

Participants

Reaction Steps

3-Aminopropanol (1.5 g, 20 mmol) was dissolved in dry DMF and treated with 3,4-dichlorobenzyl chloride (2.62 ml, 19 mmol) followed by anhydrous potassium carbonate (1.38 g, 10 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was partitioned between 1M HCl and dichloromethane, the layers separated and the aqueous phase washed with dichloromethane. The aqueous phase was adjusted to pH 12 with 1M NaOH, and extracted with dichloromethane. The organic extract was dried (MgSO4) and evaporated to afford the title compound as a colourless oil (0.96 g 22%); δH (CDCl3) 1.68-1.77 (2H, m), 2.87 (2H, t, J=5.7 Hz), 3.75 (2H, s), 3.80 (2H, t, J=5.3 Hz), 7.12-7.41 (3H, m); MS (ES+) 234 (5%, MH+), 159 (100).

Provenance & Evidence