Piperazine → 1,4-Piperazinediacetonitrile

HRID 1479399Notes

Reaction equation

HRID 1479399 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][C:15]#[N:16].[C:17](#[N:19])[CH3:18]>>[N:1]1([CH2:18][C:17]#[N:19])[CH2:6][CH2:5][N:4]([CH2:14][C:15]#[N:16])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 2581991,4-Piperazinediacetonitrile

Procedure

To a solution of piperazine (6 g, 69.77 mmol, 1.00 equiv) in acetonitrile (150 mL) was added potassium carbonate (19.2 g, 139.13 mmol, 2.00 equiv) and the mixture was stirred. To this was added dropwise a solution of 2-bromoacetonitrile (16.7 g, 140.34 mmol, 2.00 equiv) in acetonitrile (100 mL) and the suspension was stirred for 4 h at room temperature. The solids were filtered out and the resulting solution was concentrated under vacuum. The crude product was purified by re-crystallization from methanol resulting in 7.75 g (68%) of Intermediate 50.1 as a white solid.

Workup

  1. stirringthe suspension was stirred for 4 h at room temperature
  2. filtrationThe solids were filtered out
  3. concentrationthe resulting solution was concentrated under vacuum
  4. customThe crude product was purified by re-crystallization from methanol resulting in 7.75 g (68%) of Intermediate 50.1 as a white solid

Sources & evidence

ORD record
ord-d7afb7006fdf4de68c57fdee5caf9652
Source dataset
uspto-grants-2016_08
Patent number
US09408840B2

Reaction notes

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