Acrylonitrile → n,n-Bis(2-cyanoethyl)hexylamine

HRID 74710

Reaction equation

HRID 74710 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([NH2:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>>[C:1]([CH2:2][CH2:3][N:11]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2][C:1]#[N:4])#[N:4]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 8102Hexylamine

Product 1

HCID 16733110n,n-Bis(2-cyanoethyl)hexylamineYield 98.9%

Conditions

Temperature
70 °C

Procedure

20.1 g of acrylonitrile was added dropwise to an aqueous solution (150 ml) of 15.5 g of hexylamine at room temperature over 0.5 hours, and then the mixed solution was stirred at 70° C. for 3 hours. After standing to cool to room temperature, the mixed solution was extracted with 150 ml of ethyl acetate. The organic layer was separated from the solution, dried over anhydrous magnesium sulfate, and distilled off the solvent to obtain 31.4 g of a target compound as a colorless oily product.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixed solution was extracted with 150 ml of ethyl acetate
  3. customThe organic layer was separated from the solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-0d4eab3b0e8f40d185c25da15d7077e2
Source dataset
uspto-grants-2014_09
Patent number
US08830811B2

Linked notes

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