Putrescine → 3-((4-Aminobutyl)amino)propanenitrile

HRID 482176Notes

Reaction equation

HRID 482176 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7](#[N:10])[CH:8]=[CH2:9]>CO>[C:7]([CH2:8][CH2:9][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6])#[N:10]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 7855Acrylonitrile

Product 1

HCID 125483743-((4-Aminobutyl)amino)propanenitrileYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1,4-diaminobutane (8.6 g, 97.6 mmol) in methanol (3.0 ml) was added a solution of acrylonitrile (6.2 g, 116.8 mmol) in methanol (3.0 ml) at 0° C., and the mixture was stirred for 12 hours. Evaporation of the solvent in vacuo afforded N-(2'-cyanoethyl)-1,4-diaminobutane as a colorless oil (11.0 g, 80%). 1H NMR (400 MHz, CDCl3) δ: 1.45 (4H, br, --CH2 CH2 --), 2.46 (2H, t), 2.58 (2H, t), 2.62 (2H, t) and 2.84 (2H, t).

Workup

  1. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-ce6a539ffeca49d0afe50b4bb9089233
Source dataset
uspto-grants-1998_08
Patent number
US05792635

Reaction notes

Loading…