Ether hydrochloride → 2-(2,6-Dioxo-piperidin-3-yl)-4-methylaminomethyl-isoindole-1,3-dione hydrochloride

Participants

Reaction Steps

To a stirred solution of [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-methyl-carbamic acid t-butyl ester (8.1 g, 20.2 mmol) in methylene chloride (80 mL), was added 2N HCl/ether (25 mL). The mixture was stirred at room temperature overnight. The mixture was filtered, washed with CH2Cl2 (20 mL), and dried to afford 2-(2,6-dioxo-piperidin-3-yl)-4-methylaminomethyl-isoindol-1,3-dione hydrochloride (5.3 g, 77%) as an off white solid: 1H NMR (DMSO-d6) δ 11.17 (s, 1H), 9.64 (s, 2H), 8.11-7.91 (m, 3H), 5.22-5.15 (dd, J=4.9 and 12.5 Hz, 1H), 4.55 (s, 2H), 2.98-2.84 (m, 1H), 2.64-2.50 (m, 2H), 2.60 (s, 3H), 2.08-2.03 (m, 1H); 13C NMR (DMSO-d6) δ 172.69, 169.60, 167.22, 166.51, 136.40, 134.86, 131.45, 130.65, 129.20, 123.88, 48.89, 45.66, 32.39, 30.84, 21.96.

Provenance & Evidence