Water → HCID 13759791, compound

Participants

Reaction Steps

3,4,5,6-Tetrahydro-4H-pyran-4-one (0.37 g, 3.75 mmol) was added to a solution of 1,2,3,4-tetrahydroisoquinoline (0.47 mL, 3.75 mmol) in conc. HCl (0.4 mL) diluted with ice water (1.5 mL), followed by a solution of KCN (0.24 g, 3.75 mmol) dissolved in water (2 mL), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with water and the organic product was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica 60-120 mesh, eluent 6% EtOAc in petroleum ether) to afford 4-(3,4-dihydroisoquinolin-2(1H)-yl)tetrahydro-2H-pyran-4-carbonitrile (300 mg, yield 33%). 1H NMR (300 MHz, CDCl3) δ 7.19-7.11 (m, 3H), 7.07-7.05 (m, 1H), 4.10-4.04 (dt, J=12.3 Hz, 3.5 Hz, 2H), 3.87 (s, 2H), 3.76-3.68 (m, 2H), 2.97-2.91 (m, 4H), 2.28-2.23 (dd, J=13.3 Hz, 1.4 Hz, 2H), 1.93-1.84 (td, J=12.4 Hz, 4.2 Hz, 2H). MS (ESI) m/z: Calculated for C15H18N2O: 242.14. found: 243.2 (M+H)+.

Provenance & Evidence