1,2,3,4-Tetrahydroisoquinoline → 1-(3,4-Dihydroisoquinolin-2(1H)-yl)prop-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1,2,3,4-tetrahydroisoquinoline (1 g, 7.52 mmol) in anhydrous dichloromethane (10 ml) was added triethylamine (4.17 ml, 30.00 mmol) and acryloyl chloride (0.73 ml, 9.02 mmol) at 0° C. The reaction mixture was stirred at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the reaction mixture was diluted with water (50 ml) and extracted with dichloromethane (2×50 ml). The combined organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 40% ethyl acetate/pet ether as an eluent to get the desired compound as a pale brown liquid (800 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ 7.24-7.06 (m, 4H), 6.70-6.60 (m, 1H), 6.33 (dd, J=16.6, 1.5 Hz, 1H), 5.73 (dd, J=10.5, 1.7 Hz, 1H), 4.80 (s, 1H), 4.73 (s, 1H), 3.89 (t, J=5.8 Hz, 2H), 3.78 (t, J=5.8 Hz, 2H).

Provenance & Evidence