3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827304, compound

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Reaction Steps

A mixture of 3-(3,4-dimethoxyphenylamino)phthalic acid (0.59 g, 1.9 mmol) and rac-α-aminoglutarimide hydrochloride (0.32 g, 1.9 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 0.64 g of the product at 96:4 methylene chloride-methanol, in 85% yield: mp>215-217° C.; 1H NMR (CDCl3) δ 2.15-2.19 (m, 1H), 2.74-2.96 (m, 3H), 3.88 (s, 3H), 3.91 (s, 3H), 4.97 (dd, J=11.8 Hz, J=5.1 Hz, 1H), 6.78-6.81 (m, 1H), 6.85-6.91 (m, 2H), 7.16-7.21 (m, 2H), 7.45 (t, J=7.8 Hz, 1H), 7.87 (s, 1H), 8.07 (s, 1H); 13C NMR (CDCl3) δ 22.8, 31.4, 49.0, 56.0, 56.2, 108.6, 110.9, 111.8, 113.2, 116.5, 118.5, 131.7, 132.4, 135.9, 145.2, 147.1, 149.8, 167.4, 168.2, 169.4, 170.8; Anal. calcd for C21H19N3O6: C, 61.61; H, 4.68; N, 10.26. Found: C, 61.47; H, 4.52; N, 10.12.

Provenance & Evidence