Trifluoroacetic acid → (E)-1-(pyrrolidin-1-yl)-3-(1,2,3,4-tetrahydroisoquinolin-6-yl)prop-2-en-1-one trifluoro acetic acid

Participants

Reaction Steps

A solution of 125c (400 mg, 1.12 mmol) in CH2Cl2 (4 ml) was treated with TFA (1.28 g, 11.21 mmol)) at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the clear solution was concentrated under vacuum and the resultant solid was washed with diethyl ether to get the desired compound as a gummy liquid (380 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ 9.05 (bs, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.43 (d, J=15.6 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 6.99 (d, J=15.6 Hz, 1H), 4.32-4.24 (m, 2H), 3.63 (t, J=6.9 Hz, 2H), 3.39 (t, J=6.9 Hz, 4H), 3.01 (t, J=6.1 Hz, 2H), 1.98-1.89 (m, 2H), 1.88-1.76 (m, 2H).

Provenance & Evidence