Sodium Bicarbonate → HCID 59397990, compound

HRID 39743Notes

Reaction equation

HRID 39743 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[F:17][CH:18]1[CH:23]([OH:24])[CH2:22][CH2:21][NH:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(O)(=O)C.CN(C)C=O>[F:17][CH:18]1[CH:23]([OH:24])[CH2:22][CH2:21][N:20]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:16])[CH2:19]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 219737653-Fluoropiperidin-4-olHCID 59398142(7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde

Product 1

HCID 59397990HCID 59397990, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2 mL of an N,N-dimethylformamide solution containing 0.18 g of (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde and 0.1 g of 3-fluoropiperidin-4-ol, 0.14 mL of acetic acid was added, the mixture was stirred at room temperature for 1 hour, thereto was added 0.18 g of sodium triacetoxyborohydride was added, and the mixture was stirred for 30 minutes. The reaction mixture was added with an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.22 g of a brown oily substance, 1-(2-(3-fluoro-4-hydroxypiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was stirred for 30 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7e4c1d33461a43f2afa62198ea9f355b
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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