Ethyl Acetate → HCID 13587984, Verbindung

HRID 323486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323486
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.[H-].[Na+].Cl[CH2:25][C:26]1[CH:30]=[CH:29][O:28][CH:27]=1.C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[O:28]1[CH:29]=[CH:30][C:26]([CH2:25][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:27]1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 111262283-(Chloromethyl)furan

Produkt 1

HCID 13587984HCID 13587984, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Combine (1H-benzimidazol-2-yl)-(1-ethoxycarbonyl-piperidin-4-yl)amine (1.5 g, 5.2 mmol) in tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice-bath. Add sodium hydride (0.25 g, 60% n in oil, 6.24 mmol). After 3.5 hours, add 3-(chloromethyl)furan (0.91 g, 7.8 mmol). Warm to ambient temperature. After 60 hours, quench by the addition of Glauber's salt (Na2SO4 10 H2O). Evaporate to remove most of the tetrahydrofuran, dilute with ethyl acetate, and extract with a saturated aqueous sodium bicarbonate solution, water, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give (1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.32 (silica gel, ethyl acetate).

Aufarbeitung

  1. temperatureCool in an ice-bath
  2. waitAfter 60 hours
  3. customquench by the addition of Glauber's salt (Na2SO4 10 H2O)
  4. customEvaporate
  5. customto remove most of the tetrahydrofuran
  6. additiondilute with ethyl acetate
  7. extractionextract with a saturated aqueous sodium bicarbonate solution, water
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-331412c317be416cadfdbf628ea3d58a
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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