Chloroform → 5-chloro-1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine

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Reaction Steps

A solution of 1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine (3.0 g, 13.68 mmol) in acetonitrile (150 mL) was treated with N-chlorosuccinimide (2.010 g, 15.05 mmol) and stirred at room temperature for 15 minutes. The solution was poured into chloroform/saturated sodium bicarbonate (aq.) and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford 5-chloro-1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine (0.510 g, 15% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (s, 1 H), 7.01 (s, 1 H), 5.21 (s, 2 H), 4.08 (t, J=8.33 Hz, 2 H), 3.16 (s, 2 H), 2.95 (t, J=8.33 Hz, 2 H), 2.25 (s, 6 H).

Provenance & Evidence