Sodium Iodide → HCID 56599144, compound

Participants

Reaction Steps

A mixture of intermediate 48 (200 mg, 0.7 mmol) and NaI (210 mg, 1.4 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 47 (167 mg, 0.63 mmol) and anhydrous K2CO3 (386 mg, 2.8 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=5:1) to give 5-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-1H-benzo[d]imidazol-2(3H)-one (compound 24) (61 mg, 20%). 1H NMR (300 MHz, CDCl3): δ 9.59 (brs, 1H), 9.29 (brs, 1H), 7.33-7.30 (m, 2H), 7.20-7.13 (m, 1H), 6.92 (d, J=8.7 Hz, 1H), 6.65-6.59 (m, 2H), 3.94-3.91 (m, 2H), 3.15-3.04 (m, 3H), 2.51-2.49 (m, 2H), 2.15 (t, J=11.1 Hz, 2H), 1.90-1.74 (m, 8H). HPLC: 99%, RT 2.332 min. MS (ESI) m/z 434.0 [M+H]+. mp: 180-182° C.

Provenance & Evidence