5-Nitrofurfural → HCID 16730730, compound

HRID 507336Notes

Reaction equation

HRID 507336 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:24])[CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:3][CH:2]=1.[N+:25]([C:28]1[O:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O-:27])=[O:26].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(O)(=O)C.ClCCl>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:24])[CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH2:32][C:31]3[O:34][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=3)[CH2:20][CH2:19]2)=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 127745-NitrofurfuralHCID 5049666Sodium triacetoxyborohydrideHCID 167304831-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol

Product 1

HCID 16730730HCID 16730730, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0c6062099b2d4eb18641311a6de49452
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

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