p-Toluenesulfonic acid → 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

Participants

Reaction Steps

569 mg (2.62 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.3 ml (2.65 mmol) of 3-chlorobenzaldehyde and 0.03 ml (0.34 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 30 ml of benzene overnight while water was removed. Ethyl acetate was added to the reaction mixture, and the product was washed with 1 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-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide. 20 ml of 2-propanol and 260 mg (2.62 mmol) of 4-amino-3-pentene-2-on were added to the product, and they were heated at 80° C. under stirring for 3 days. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (ethyl acetate) to obtain the title compound.

Provenance & Evidence