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

HRID 68330

Reaction equation

HRID 68330 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-88aed81520ce4af292ff71b46de4380a
Source dataset
uspto-grants-2014_09
Patent number
US08822452B2

Linked notes

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