5-Nitrofurfural → 1-(9H-carbazol-4-yloxy)-3-{4-[(5-nitro-2-furyl)methyl]piperazin-1-yl}propan-2-ol

To a mixture of 1-(9H-carbazol-4-yloxy)-3-piperazin-1-yl propan-2-ol (0.5 g 1.54 mmol) in THF (10 mL), was added 2-3 drops of glacial acetic acid, followed by 5-nitrofurfural (0.325 g, 2.3 mmol). To the above solution Na(OAc)3BH (0.98 g, 4.6 mmol) was added carefully at room temperature and the reaction mixture was stirred at room temperature for 6 hours. Subsequently the reaction mixture was diluted with dichloromethane (50 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, concentrated, and purified by silica gel column chromatography using dichloromethane/MeOH (9:1) to afford the title compound as a yellow colored solid (0.2 g, 29% yield) with m.p.: 54-59° C. 1H NMR (400 MHz, CDCl3): δ 2.40-2.65 (m, 6H), 2.70-2.80 (m, 4H), 3.67 (s, 2H), 4.20-4.25 (m, 1H), 4.27-4.34 (m, 2H) 6.49 (d, 1H, J=3.6 Hz), 6.67 (d, 1H, J=8.0 Hz), 7.06 (d, 1H, J=8.0 Hz), 7.20-7.50 (m, 5H), 8.27 (s, 1H), and 8.30 (d, 1H, J=8 Hz). MS m/z: 451 (M+1).

1. washwashed with water and brine solution
2. dry with materialThe organic layer was dried over anhydrous Na2SO4
3. concentrationconcentrated
4. custompurified by silica gel column chromatography

ORD-Eintrag

ord-0c6062099b2d4eb18641311a6de49452

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07786142B2