Putrescine → 3,3'-(Tetramethylendiimino)dipropionitrile

HRID 2099913Notes

Reaction equation

HRID 2099913 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][NH:6][CH2:4][CH2:3][C:2]#[N:1])#[N:10]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 7855Acrylonitrile

Product 1

HCID 108888183,3'-(Tetramethylendiimino)dipropionitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1,4-diaminobutane 1 (n=4; 25.0 g, 0.28 mol) in methanol (50 mL) was added dropwise a solution of acrylonitrile (31.6 g, 0.60 mmol) in methanol (25 mL) at 0° C. After the addition the mixture was allowed to come to room temperature and then stirred for 18 h. Finally, the solvent was removed in vacuo, to give the diamine 2 as a pale yellow liquid, (57.0 g, quant.).

Workup

  1. additionAfter the addition the mixture
  2. customto come to room temperature
  3. customFinally, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-2b6ce6edd4364d8fb2d27b95b9e6e780
Source dataset
uspto-grants-2009_08
Patent number
US07569720B2

Reaction notes

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