Triethylamine → 4-Bromo-1-(octahydroquinolin-1-yl)butan-1-one

HRID 68330

Reaktionsgleichung

Reaktionsgleichung von HRID 68330
CCN(CC)CC.[Br:8][CH2:9][CH2:10]CCC(Cl)=O.[NH:16]1[CH:25]2[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18][CH2:17]1.CCO[C:29]([CH3:31])=[O:30]>>[Br:8][CH2:9][CH2:10][CH2:31][C:29]([N:16]1[CH:25]2[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18][CH2:17]1)=[O:30]

Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 92911DecahydroquinolineHCID 5211735-Bromovaleryl chloride

Produkt 1

HCID 667946444-Bromo-1-(octahydroquinolin-1-yl)butan-1-one

Versuchsvorschrift

1.37 mL (9.9 mmol) of Et3N and 0.5 mL (4.5 mmol) of 5-bromovaleric acid chloride are added to a solution of 1 mL (4.0 mmol) of the decahydroquinoline in AcOEt. The resulting solution is kept under stirring for 18 h at rt. The solution is then washed with water, and the water re-extracted twice with AcOEt. The pooled organic phases are sequentially washed with 5% solution of NaHCO3, 1N HCl and saturated ammonium chloride solution. Finally the organic phase is dried over anhydrous Na2SO4, it is filtered and the solvent is evaporated under reduced pressure. 1.2 g of a yellow oil, which was used without subsequent purification, are obtained.

Aufarbeitung

  1. washThe solution is then washed with water
  2. extractionthe water re-extracted twice with AcOEt
  3. washThe pooled organic phases are sequentially washed with 5% solution of NaHCO3, 1N HCl and saturated ammonium chloride solution
  4. dry with materialFinally the organic phase is dried over anhydrous Na2SO4, it
  5. filtrationis filtered
  6. customthe solvent is evaporated under reduced pressure
  7. custom1.2 g of a yellow oil, which was used without subsequent purification
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-88aed81520ce4af292ff71b46de4380a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822452B2

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