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

HRID 39217

Reaktionsgleichung

Reaktionsgleichung von HRID 39217
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-4385fe3b05a5409db891b352d1f7b58c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524894B2

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