Dimethylformamide → (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

HRID 323509

Reaktionsgleichung

Reaktionsgleichung von HRID 323509
[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.CN(C)C=O.[H-].[Na+].[Si:29]([O:36][CH2:37][CH2:38]I)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>CO.ClCCl.ClCCl.O1CCCC1>[Si:29]([O:36][CH2:37][CH2:38][N: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)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

Produkt 1

HCID 22009292(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Combine (1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (4.00 g, 13.87 mmol) and dimethylformamide (12 mL) and tetrahydrofuran (60 mL). Cool in an ice-bath. Add sodium hydride (24 mg, 15.3 mmol). After 24 hours, add 2-(t-butyldimethylsilyloxy) ethyl iodide (3.97 g, 13.87 mmol). After 60 hours, add ice to quench the reaction. Evaporate the quenched reaction mixture in vacuo to remove most of the tetrahydrofuran. Partition the evaporated reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane and then 5% methanol/dichloromethane to give (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.14 (silica gel, 40% ethyl acetate/dichloromethane).

Aufarbeitung

  1. temperatureCool in an ice-bath
  2. waitAfter 60 hours
  3. additionadd ice
  4. customto quench
  5. customthe reaction
  6. customEvaporate
  7. customthe quenched reaction mixture in vacuo
  8. customto remove most of the tetrahydrofuran
  9. customPartition
  10. customthe evaporated reaction mixture between water and ethyl acetate
  11. customSeparate the layers
  12. extractionextract the organic layer three times with water
  13. dry with materialDry the organic layer over MgSO4
  14. filtrationfilter
  15. customevaporate in vacuo
  16. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-e125e3d17ab74f5eac4e714d3a6ea61f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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