3-Aminopropionitrile → 3-(Di-5-hexenyl)aminopropionitrile

HRID 18382

Reaction equation

HRID 18382 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]#[N:5].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.CN(C)C=O>[CH2:7]([N:5]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH2:7])[CH2:4][CH2:3][C:2]#[N:1])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

7

Reactant 4

HCID 16473-AminopropionitrileHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 759066-Bromo-1-hexene

Product 1

HCID 121366273-(Di-5-hexenyl)aminopropionitrileYield 67%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (28 ml) was added to 3-aminopropionitrile (0.98 g, 14 mmol), and the mixture was stirred at room temperature. 6-Bromo-1-hexene (5.0 g, 31 mmol), sodium iodide (11 g, 73 mmol) and potassium carbonate (5.8 g, 42 mmol) were added to the mixture, and the whole was stirred overnight. The reaction mixture was diluted with diethyl ether (100 ml), and the whole was washed with water (100 ml, twice) and saturated brine (50 ml) successively. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-(di-5-hexenyl)aminopropionitrile (2.2 g, 66%) as a colorless oily matter.

Workup

  1. stirringthe whole was stirred overnight
  2. washthe whole was washed with water (100 ml
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac0a6b6c606f4b0f9a11ff9d59f587bb
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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