Ethanol → N-(Hex-5-en-1-yl)hex-5-en-1-amine

HRID 1393144Notes

Reaction equation

HRID 1393144 reaction equation
C(O)C.[OH-].[K+].[CH2:6]([N:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])CCC#N)[CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].O>C(Cl)(Cl)Cl>[CH2:6]([NH:12][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 121366273-(Di-5-hexenyl)aminopropionitrile

Product 1

HCID 15640332N-(Hex-5-en-1-yl)hex-5-en-1-amineYield 21%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Next, ethanol (8.6 ml) and potassium hydroxide (0.85 g, 13 mmol) were added to 3-(di-5-hexenyl)aminopropionitrile (2.0 g, 8.6 mmol), and the mixture was refluxed for 7.5 hours. The reaction mixture was allowed to stand, and then water (150 ml) and chloroform (150 ml) were added to the reaction mixture. Layers were separated, and the organic layer was dried over sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography to give 0.32 g (21%) of the titled compound as a pale yellow oily matter.

Workup

  1. temperaturethe mixture was refluxed for 7.5 hours
  2. customLayers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-b0e238bf03ed47fd90d5b496e1dc09a9
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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