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Sodium Bicarbonate → HCID 59398427, Verbindung

HRID 39793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 39793
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 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

Produkt 1

HCID 59398427HCID 59398427, VerbindungAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7181126977fe4d56b3e830d63a85ff96
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524738B2

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