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

HRID 18383Notes

Reaction equation

HRID 18383 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 obtained mixture was refluxed for 7.5 hours. The reaction mixture was allowed to stand, then water (150 ml) and chloroform (150 ml) were added to the reaction mixture. After separation, the organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography to give the target compound (0.32 g, 21%) as a pale yellow oily matter.

Workup

  1. temperaturethe obtained mixture was refluxed for 7.5 hours
  2. customAfter separation
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-83150b480f524dde80da8571a47199d3
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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