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Sodium hydride → (1-(4-oxopentyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

HRID 323345
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 323345
[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][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[H-].[Na+].Cl[CH2:27][CH2:28][CH2:29][C:30](=[O:32])[CH3:31].[Cl-].[NH4+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+].CO.ClCCl.CN(C)C=O.O1CCCC1>[O:32]=[C:30]([CH3:31])[CH2:29][CH2:28][CH2:27][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][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 799932-Pentanone, 5-chloro-2×HCID 22036999tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate

Produkt 1

HCID 22009233(1-(4-oxopentyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Reagenzien, Katalysatoren, Lösungsmittel

5
HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (3.5 mmol) and tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice bath and add sodium hydride (0.21 g, 60% in oil, 5.22 mmol). After 1 hour, add 5-chloropentan-2-one, ethylene ketal (0.79 mL, 5.22 mmol) and tetra-n-butylammonium bromide (112 mg, 0.35 mmol) and warm to ambient temperature. Heat to reflux. After 18 hours, cool, add sodium hydride (0.1 g) and 5-chloropentan-2-one, ethylene ketal (0.50 mL) and again heat to reflux. After 24 hours, cool in a dry-ice/acetone bath and add a saturated aqueous solution of ammonium chloride. Warm to ambient temperature and dilute the reaction mixture with a saturated aqueous solution of sodium bicarbonate. Concentrate in vacuo to remove most to the tetrahydrofuran and extract three times with ethyl acetate. Extract the combined organic layers with water and then brine, dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane/0.1% saturated aqueous ammonia solution to give (1-(4-oxopentyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine, ethylene ketal.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. temperatureHeat to reflux
  3. waitAfter 18 hours
  4. temperaturecool
  5. temperatureagain heat to reflux
  6. waitAfter 24 hours
  7. temperaturecool in a dry-ice/acetone bath
  8. temperatureWarm to ambient temperature
  9. concentrationConcentrate in vacuo
  10. customto remove most to the tetrahydrofuran
  11. extractionextract three times with ethyl acetate
  12. extractionExtract the combined organic layers with water
  13. dry with materialbrine, dry the organic layer over Na2SO4
  14. filtrationfilter
  15. customevaporate in vacuo
  16. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-d89fd8746f344cdc9a54815184619c2f
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06211199B1

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