Triethylamine → 6-{2-Oxo-4-[2-(1-oxo-3,4-dihydro-1H-isochromen-6-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Participants

Reaction Steps

A mixture of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (51 mg, 0.17 mmol) and triethylamine (65 mg, 0.64 mmol) was dissolved in dichloroethane then (1-oxo-3,4-dihydro-1H-isochromen-6-yl) acetaldehyde (60 mg, 0.26 mmol) was added followed by sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was stirred at RT for 16 hours. The reaction mixture was poured into water then extracted with dichloromethane. The organic layer was washed with brine then dried over Na2SO4, filtered and concentrated. The compound was purified by preparative TLC plate to yield the title product. 1H-NMR (500 MHz, CDCl3) δ ppm 8.07 (d, J=7.8 Hz, 1H), 7.43 (s, 1H), 7.42 (d, J=7.5 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 7.18 (d, J=7.61 Hz, 1H), 7.14 (s, 1H), 4.90 (b, 1H), 4.57 (t, J=5.7 Hz, 2H), 3.27-3.36 (m, 4H), 3.08 (t, J=5.8 Hz, 2H), 3.02-2.74 (m, 10H), 2.01 (b, 1H), 1.92-1.95 (m, 1H).

Provenance & Evidence