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

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

Reactant 2

HCID 7855Acrylonitrile

HCID 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

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

Sources & evidence

ORD record: ord-0d4eab3b0e8f40d185c25da15d7077e2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08830811B2

Reaction notes

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