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

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).

1. customIn the course of the reaction a white crystalline solid forms
2. extractionThe free amine is extracted three times with AcOEt
3. dry with materialThe combined organic phases are dried over Na2SO4
4. customEvaporation of the solvent in vacuo
5. customyields a yellow oil
6. customIt is purified by chromatography on silica-gel (dichloromethane/MeOH, 95:5)

ORD record

ord-b8b705db62fe43f4bf5bfea7ed7bfe8e

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273740B2