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

Temperature

27.5 °C

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).

1. stirringAfter 16 h of stirring
2. extractionextracted with dichloromethane (2×50 ml)
3. washThe combined organic layers were washed with brine (50 ml)
4. dry with materialby drying over anhydrous Na2SO4
5. filtrationfiltering
6. customThe filtrate was rotary evaporated
7. customto get residue which
8. customwas purified by column chromatography
9. additiona mixture of 40% ethyl acetate/pet ether as an eluent

ORD record

ord-67a225295adc489ab4839dd04c6d3e7a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062002B2