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Sodium Bicarbonate → HCID 59398427, compound

HRID 2193163
Notes
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Reaction equation

HRID 2193163 reaction equation
[O:1]=[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH:13]=O.[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([C:24]2[CH:33]=[CH:32][C:27]3[O:28][CH2:29][CH2:30][O:31][C:26]=3[CH:25]=2)=[O:23])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)C.C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:1]=[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([C:24]2[CH:33]=[CH:32][C:27]3[O:28][CH2:29][CH2:30][O:31][C:26]=3[CH:25]=2)=[O:23])[CH2:17][CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 28938004N-(piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-carboxamideHCID 59397888(2-oxoquinoxalin-1(2H)-yl)acetaldehyde

Product 1

HCID 59398427HCID 59398427, compoundYield 74.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent
HCID 3283Diethyl EtherSolvent
HCID 6212ChloroformSolvent
HCID 6344DichloromethaneSolvent

Procedure

To 3 mL of dichloromethane solution containing 70 mg of (2-oxoquinoxalin-1(2H)-yl)acetaldehyde, 98 mg of N-(piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-carboxamide and 21 μl of acetic acid were added and stirred at room temperature for 2 hours. To the reaction mixture, 0.12 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=20:1], and to the residue thus obtained, diethyl ether was added, and the resulting solid was filtered to give 0.12 g of N-(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-carboxamide as a light brown solid.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]
  10. customto the residue thus obtained
  11. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-0e195b181f4c4433a4540c3fbfdd7fdd
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329694B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes