3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827281, compound

Participants

Reaction Steps

A mixture of 3-(3,4-methylenedioxyphenylamino)phthalic acid (0.50 g, 1.7 mmol) and rac-α-aminoglutarimide hydrochloride (0.29 g, 1.7 mmol) in pyridine (10 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was chromatographed using a methylene chloride-methanol gradient, eluting 0.52 g of the product at 95:5 methylene chloride-methanol, in 80% yield: mp>260° C.; 1H NMR (DMSO-d6) δ 2.03-2.08 (m, 1H), 2.57-2.63 (m, 2H), 2.83-2.96 (m, 1H), 5.11 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 6.04 (s, 2H), 6.80 (dd, J=8.3 Hz, J=1.9 Hz, 1H), 6.92-6.95 (m, 2H), 7.16-7.22 (m, 2H), 7.56 (t, J=7.8 Hz, 1H), 8.25 (s, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 101.3, 105.5, 108.6, 110.9, 112.7, 116.7, 118.9, 132.3, 133.2, 136.2, 144.1, 144.5, 147.9, 167.1, 168.3, 170.0, 172.8; Anal. calcd for C20H15N3O6.0.2H2O: C, 60.51; H, 3.91; N, 10.58. Found: C, 60.49; H, 3.62; N, 10.50.

Provenance & Evidence