Cyclopentylamine → 1-(2-chloroethyl)-3-cyclopentylurea

Participants

Reaction Steps

A 0° C. solution of cyclopentylamine (4.63 mL, 47.0 mmol) in THF (235 mL) was treated drop-wise with 2-chloroethyl isocyanate (4.41 mL, 51.7 mmol) which was allowed to warm to RT, then concentrated to dryness. The solid was suspended in toluene and concentrated again to dryness to afford 1-(2-chloroethyl)-3-cyclopentylurea (8.95 g, 100%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.01 (d, J=7.3 Hz, 1 H), 5.91 (t, J=5.8 Hz, 1 H), 3.85-3.76 (m, 1 H), 3.54 (t, J=6.2 Hz, 2 H), 3.27 (q, J=6.1 Hz, 2 H), 1.78-1.69 (m, 2 H), 1.62-1.53 (m, 2 H), 1.51-1.42 (m, 2 H), 1.30-1.20 (m, 2 H); MS (ESI) m/z: 191.1 (M+H+).

Provenance & Evidence