Acrylonitrile → N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane

HRID 3087

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[CH3:5][N:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11]>CO>[C:1]([CH2:2][CH2:3][NH:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH3:12])[CH3:5])#[N:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of acrylonitrile (1.17 g, 22.07 mmol) in methanol (1.0 ml) was added dropwise to a solution of N,N-dimethyl-1,4-diaminobutane 322 (2.1 g, 18.42 mmol) in methanol (1.0 ml) at 0° C., and the mixture was stirred at 0° C. for sixteen hours. Evaporation of the solvent in vacuo afforded almost pure N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane 323 as a colorless oil (2.5 g, 80% yield based on 322). 1H NMR (400 MHz, CDCl3) δ: 1.45 (4H, m, --CH2 --CH2 --CH2 --CH2 --), 2.15 (6H, s, --N(CH3)2), 2.22 (2H, t, --CH2N), 2.47 (2H, t, --CH2CH2CN), 2.60 (2H, t, --CH2CH2NH--), 2.88 (2H, t, --CH2CH2NH--), 3.37 (1H, s, --NH).

Workup

customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-84edcdeb710843f298afe85eff4bc91e
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733899

Linked notes

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