p-Toluenesulfonic acid → HCID 54137441, compound

Participants

Reaction Steps

541 mg (2.49 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 328 mg (2.50 mmol) of 3-cyanobenzaldehyde and 0.2 ml (2.02 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluene Sulfonic acid in 30 ml of benzene overnight while water was removed. Ethyl acetate was added to the reaction mixture, which was washed with 2 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2-acetyl-3-(3-cyanophenyl)-N-(3-phenyl-2-propene-1-yl) acrylamide. This product was heated together with 387 mg (2.5 1 mmol) of 2-cyanoethyl 3-aminocrotonate at 80° C. under stirring in 20 ml of 2-propanol for four days. 2-Propanol was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (chloroform/methanol=100/1) to obtain the title compound.

Provenance & Evidence