Acrylonitrile → 4-(Methylsulfonyl)-1-piperazinepropanenitrile

HRID 1803929Notes

Reaction equation

HRID 1803929 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].[C:11](#[N:14])[CH:12]=[CH2:13]>CO>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:13][CH2:12][C:11]#[N:14])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 7091611-(Methylsulfonyl)piperazine

Product 1

HCID 287054204-(Methylsulfonyl)-1-piperazinepropanenitrileYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(methylsulfonyl)piperazine (1 g, 6.09 mmol) in MeOH (11 mL) at 0° C. is added acrylonitrile (0.402 mL, 6.09 mmol). The reaction mixture is concentrated in vacuo and the resulting residue diluted with 5 mL of water and extracted with EtOAc (3×25 mL). The combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue is purified over silica (2% MeOH in CH2Cl2) to afford 1.1 g (99% yield) of the desired compound. 1H NMR (CDCl3, 300 MHz) δ2.56 (t, J=6.9 Hz, 2H), 2.66 (t, J=4.8 Hz, 4H), 2.76 (t, J=6.9 Hz, 2H), 2.81 (s, 3H), 3.30 (t, J=4.8 Hz, 4H). MS (ESI, pos. ion) m/z: 218 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe resulting residue diluted with 5 mL of water
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified over silica (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b00eb9246b9044ef9da712759a285ac1
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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