Acetic Acid → 5-((2-Oxo-4-(2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Participants

Reaction Steps

A solution of 5-(Piperazin-1-ylmethyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile (30 mg, 0.11 mmol) in 2 mL DCM/MeOH (1/1) was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (0.11 mmol), AcOH (6.6 mg, 0.11 mmol) and the reaction mixture was stirred for 2 hours, and then NaBH3CH (14 mg, 0.22 mmol) was added. The resulting mixture was stirred overnight at ambient temperature. The product was purified by prep-TLC (DCM/MeOH=20:1) to afford the desired product. 1H-NMR (400 MHz, MeOD) δ ppm 7.76 (d, J=8.0 Hz, 1H), 7.44-7.51 (m, 4H), 7.24 (t, J=8.0 Hz, 1H), 5.33 (s, 2H), 3.74-3.80 (m, 1H), 3.32-3.45 (m, 3H), 3.22-3.27 (m, 1H), 3.20 (d, J=2.4 Hz, 2H), 2.96-3.03 (m, 3H), 2.73-2.85 (m, 5H), 1.93-2.02 (m, 1H), 1.75-1.84 (m, 3H).

Provenance & Evidence