Piperazine → 1,4-Piperazinedipropanenitrile

HRID 557981Notes

Reaction equation

HRID 557981 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7](#[N:10])[CH:8]=[CH2:9]>O>[N:1]1([CH2:9][CH2:8][C:7]#[N:10])[CH2:6][CH2:5][N:4]([CH2:9][CH2:8][C:7]#[N:10])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 7855Acrylonitrile

Product 1

HCID 778081,4-PiperazinedipropanenitrileYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of piperazine (1 g, 11.6 mmol) and acrylonitrile (1.6 g, 30.16 mmol, 2.6 eq) in water (10 cm3) were stirred at room temperature for 5 hours, after which the mixture was extracted with dichloromethane (2×50 cm3). The organic extracts were evaporated under reduced pressure to give the pure doubly cyanoethylated compound 3,3′-(piperazine-1,4-diyl)dipropanenitrile (2.14 g, 94.7%) as a white solid, mp 66-67° C.

Workup

  1. extractionafter which the mixture was extracted with dichloromethane (2×50 cm3)
  2. customThe organic extracts were evaporated under reduced pressure

Sources & evidence

ORD record
ord-c99864d71f994e6489648adacca3af82
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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