Sodium Iodide → HCID 56597093, compound

Participants

Reaction Steps

A mixture of intermediate 21 (103 mg, 0.35 mmol) and NaI (105 mg, 0.7 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 47 (142 mg, 0.53 mmol) and anhydrous K2CO3 (194 mg, 1.4 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH 30:1) to give 7-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-3,4-dihydroisoquinolin-1(2H)-one (compound 33) (108 mg, 69%). 1H NMR (300 MHz, CDCl3): δ 7.58 (d, J=2.1 Hz, 1H), 7.23-7.11 (m, 5H), 7.02-6.99 (m, 1H), 6.05 (s, 1H), 4.05 (t, J=6.0 Hz, 2H), 3.56-3.53 (m, 2H), 3.15-3.06 (m, 3H), 2.93 (t, J=6.6 Hz, 2H), 2.51 (m, 2H), 2.18 (m, 2H), 1.82 (m, 8H). HPLC: 99%, RT 2.746 min. MS (ESI) ink 447.2 [M+H]+. mp: 113-114° C.

Provenance & Evidence