Chloroacetyl chloride → HCID 67229950, compound

Participants

Reaction Steps

Triethylamine (0.7 g, 6.5 mmol) was added to a stirred suspension of 3-(4-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.8 g, 2.6 mmol) in THF (50 mL). After stirring for 5 minutes, chloroacetyl chloride (0.4 g, 3.6 mmol) was added slowly. The resulting brown suspension was refluxed overnight. The mixture was cooled and quenched with methanol (1 mL). The mixture was concentrated, and the solid was stirred with 0.5N HCl (30 mL). The mixture was filtered, and the solid was slurried with ethanol (15 mL) to give 2-chloro-N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-acetamide (0.7 g, 76%): 1H NMR (DMSO-d6) δ 1.99-2.04 (m, 1H), 2.35-2.65 (m, 2H), 2.85-2.94 (m, 1H), 4.19 (s, 2H, CH2), 5.10-5.18 (dd, J=5.1 and 13.3 Hz, 1H, CH), 7.50-7.66 (m, 3H), 8.80 (t, J=5.7 Hz, 1H, NH), 11.01 (s, 1H, NH).

Provenance & Evidence