Dimethylformamide → HCID 18509504, compound

Participants

Reaction Steps

N-(4-tert-butylbenzyl)methylamine (1.25 g; 7.04 mmol) and potassium carbonate (1.95 g; 14.1 mmol) were added to N,N-dimethylformamide (30 ml). While the mixture was stirred in an ice bath, 3′-bromomethylacetophenone (1.50 g; 7.04 mmol) in N,N-dimethylformamide (10 ml) was added dropwise. After completion of the addition, the mixture was removed from the ice bath, and stirred for 1 hour at room temperature. Reaction was stopped by pouring the mixture into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform), to thereby yield 1.42 g of the target compound as pale yellow oily matter (yield: 65.2%).

Provenance & Evidence