Sodium Iodide → 7-(5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyloxy)-3,4-dihydroquinolin-2(1H)-one

A mixture of intermediate 4 (110 mg, 0.34 mmol) and NaI (102 mg, 1.36 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 55 (117 mg, 0.51 mmol) and anhydrous K2CO3 (188 mg, 1.36 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred for 4 h. 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-(5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyloxy)-3,4-dihydroquinolin-2(1H)-one (compound 39) (112 mg, 81%). 1H NMR (300 MHz, CDCl3): δ 7.92 (brs, 1H), 7.06-6.85 (m, 5H), 6.52 (d, J=6.6 Hz, 1H), 6.31 (s, 1H), 3.98-3.94 (m, 2H), 3.86 (s, 3H), 3.12 (br, 4H), 2.92-2.87 (m, 2H), 2.69-2.59 (m, 6H), 2.52-2.47 (m, 2H), 1.82-1.72 (m, 4H). HPLC: 99%, RT 2.100 min. MS (ESI) m/z 410.2 [M+H]+.

1. temperaturewas heated
2. temperatureto reflux for 30 min
3. temperatureThe resulting mixture was heated
4. temperatureto reflux
5. customPrecipitated crystals
6. filtrationwere filtered off
7. customthe filtrate was evaporated under reduced pressure
8. extractionThe residue was extracted with EtOAc
9. washThe combined EtOAc layers were washed with brine
10. dry with materialdried over anhydrous Na2SO4
11. concentrationconcentrated in vacuo
12. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1)

ORD record

ord-bb981dae42af4c788791757294f961c9

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156822B2