3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827277, compound

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Reaction Steps

A mixture of 3-phenylaminophthalic acid (0.52 g, 2.0 mmol) and rac-α-aminoglutarimide hydrochloride (0.33 g, 2.0 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 hexanes-ethyl acetate gradient, eluting 0.60 g of the product at 4:6 hexanes-ethyl acetate, in 83% yield: mp 214-216° C.; 1H NMR (DMSO-d6) δ 1.99-2.09 (m, 1H), 2.53-2.64 (m, 2H), 2.84-2.97 (m, 1H), 5.13 (dd, J=12.6 Hz, J=5.4 Hz, 1H), 7.11-7.16 (m, 1H), 7.25 (d, J=7.0 Hz, 1H), 7.31-7.45 (m, 5H), 7.61 (t, J=7.8 Hz, 1H), 8.45 (s, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 112.0, 113.4, 119.4, 121.9, 124.0, 129.4, 132.5, 136.2, 139.4, 142.8, 167.0, 168.3, 170.0, 172.8; Anal. calcd for C19H15N3O4: C, 65.32; H, 4.33; N, 12.03. Found: C, 64.93; H, 4.33; N, 11.79.

Provenance & Evidence