Sodium Bicarbonate → HCID 59398372, compound

HRID 40019Notes

Reaction equation

HRID 40019 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[CH3:23][O:24][C:25]1[C:30]2[O:31][CH2:32][CH2:33][O:34][C:29]=2[CH:28]=[C:27]([CH:35]=O)[CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14]([N:13]=[CH:12][C:11](=[O:22])[N:10]2[CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][CH:2]([NH:1][CH2:35][C:27]3[CH:26]=[C:25]([O:24][CH3:23])[C:30]4[O:31][CH2:32][CH2:33][O:34][C:29]=4[CH:28]=3)[CH2:7][CH2:6]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 6065788-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 593978381-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 59398372HCID 59398372, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To 10 mL of a chloroform solution containing 598 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 384 mg of 8-methoxy-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde, 113 μL of acetic acid was added, and stirred at room temperature for 1 hour. To the reaction mixture, 639 mg of sodium triacetoxyborohydride was added, and stirred for 2 hours. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution was added, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=5:1] to give 492 mg of 7-methoxy-1-(2-(4-((8-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl)methylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as a pale yellow solid.

Workup

  1. additionwas added
  2. stirringstirred for 2 hours
  3. customthe solvent was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=5:1]

Sources & evidence

ORD record
ord-c2447bff3ab24a42871000afef6cf4aa
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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