Triethylamine → 2-Propanol, reaction products with ammonia, distn. residues

Participants

Reaction Steps

A solution of cyclopropanecarbaldehyde (4.6 ml, 0.061 mol), (3-amino-propyl)-carbamic acid benzyl ester hydrochloride (15 g, 0.061 mol) and triethylamine (8.5 ml, 0.061 mol) in methanol (244 ml) was stirred at room temperature overnight. Sodium borohydride (3.7 g, 0.098 mol) was added and the reaction mixture was stirred at room temperature for 4 h. Sodium hydroxide solution (1N) was added and the reaction was concentrated to remove methanol. The residue was extracted with ethyl acetate and the combined extracts were washed with brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, chloroform saturated with ammonia-2-propanol, 99.5:0.5) gave [3-(cyclopropylmethyl-amino)-propyl]-carbamic acid benzyl ester; 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 5H), 5.60 (bs, 1H), 5.10 (s, 2H), 3.30 (q, 2H, J=6.1 Hz), 2.70 (t, 2H, J=6.5 Hz), 2.43 (d, 2H, J=6.8 Hz), 1.67 (m, 2H), 0.92 (m, 1H), 0.46 (m, 2H), 0.099 (q, 2H, J=4.9 Hz).

Provenance & Evidence