Phenethylamine → 3-Chloro-N-(2-phenylethyl)propan-1-amine

Participants

Reaction Steps

A mixture of phenethylamine (7.1 g, 7.38 ml, 58.5 mmol) and bromochloropropane (3.07 g, 1.93 ml, 19.5 mmol) in acetonitrile (15 ml) is stirred for 16 h. In the course of the reaction a white crystalline solid forms. Saturated aqueous NaHCO3 solution is added to adjust the pH to 9-10. The free amine is extracted three times with AcOEt. The combined organic phases are dried over Na2SO4. Evaporation of the solvent in vacuo yields a yellow oil. It is purified by chromatography on silica-gel (dichloromethane/MeOH, 95:5), yielding the title compound (1.02 g) in 26% as a slightly yellow oil which crystallizes on standing: 1H-NMR (CDCl3): δ (ppm) 1.91 (quint., 2H, CH2CH2N), 2.75 (m, 4H), 2.81-2.89 (m, 2H), 3.59 (t, 2H, CH2Cl), 7.20 (m, 3Harom), 7.24-7.32 (m, 2Harom).

Provenance & Evidence