Hydrochloric Acid → (R)-1-(1-phenylethyl)urea

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-1-phenylethylamine (1.00 g, 8.25 mmol) in water (4 mL) was treated with a 1 M solution of HCl in water (8.5 mL, 8.5 mmol) followed by potassium cyanate (3.35 g, 41.2 mmol). The reaction mixture was warmed to 80° C. for 1 hour and cooled. The mixture was neutralized with saturated NaHCO3 and extracted with ethyl acetate and 2-methyltetrahydrofuran. The combined organic phase was dried (Na2SO4), filtered and concentrated. Chromatography on SiO2 (0-10% MeOH/DCM) gave the desired urea product (1.32 g, 8.04 mmol; 97%) as a white solid. MS ESI calc'd for C9H12N2O [M+H]+ 165, found 165. 1H NMR (600 MHz, DMSO-d6) δ 7.23-7.28 (m, 4 H), 7.17 (t, J=6.7 Hz, 1 H), 6.38 (d, J=7.9 Hz, 1 H), 5.38 (br s, 2 H), 4.65 (m, 1 H), 1.26 (d, J=7.1 Hz, 3 H).

Provenance & Evidence