3-Aminopiperidine-2,6-dione hydrochloride → [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-urea

Participants

Reaction Steps

A mixture of 3-ureidomethyl-phthalic acid (1.5 g, 6.1 mmol) and α-amino-glutarimide hydrochloride (1.0 g, 6.1 mmol) in pyridine (15 mL) was refluxed for 5 hours. The mixture was concentrated and the residue was stirred with water (20 mL). The solid was slurried with hot methanol to give [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-urea (0.7 g, 36%): mp 292-294° C.; 1H NMR (DMSO-d6) δ 2.04-2.08 (m, 1H), 2.50-2.63 (m, 2H), 2.83-2.98 (m, 1H), 4.61 (d, J=6.1 Hz, 2H, CH2), 5.11-5.18 (m, dd, J=5.3 and 12.5 Hz, 1H, CH), 5.71 (s, 2H, NH2), 6.57 (t, J=6.0 Hz, 1H, NH), 7.70-7.87 (m, 3H, Ar), 11.15 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.98, 30.92, 38.66, 48.82, 121.63, 126.95, 131.50, 133.32, 134.61, 141.06, 158.65, 167.04, 167.57, 169.82, 172.76; Anal. calcd. for C15H14N4O5: C, 54.44; H, 4.27; N, 16.96. Found: C, 54.47; H, 4.17; N, 16.76.

Provenance & Evidence