Dimethylamine → HCID 22177243, compound

Participants

Reaction Steps

To a solution of 2-(4iodophenyl)-4oxobutyronitrile (2.03 g, 7.1 mmol) in ClCH2CH2Cl (50 mL) was added dimethylamine (14.3 mL, 2M in THF, 28.6 mmol, 4 eq) and the mixture was left stirring at room temperature for 1 h. Na(OAc)3BH (6.04 g, 28.6 mmol, 4 eq) was added and the mixture was stirred at room temperature for 16 h. The reaction was quenched by adding aqueous saturated NaHCO3 (50 mL) and the mixture was extracted with EtOAc (50 mL×3). The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography (50% EtOAc/hexanes) to give 4dimethylamino-2-(4iodophenyl)-butyronitrile as a dark brown solid, 2.09 g (94%). 1H NMR (300 MHz, CDCl3): δ 7.83 (d, 2H), 7.22 (d, 2H), 4.10 (t, 1H), 2.56 (m, 1H), 2.41 (m, 1H), 2.34 (s, 6H), 2.20 (m, 1H), 2.05 (m, 1H).

Provenance & Evidence