Acrylonitrile → HCID 24710353, compound

HRID 1803927Notes

Reaction equation

HRID 1803927 reaction equation
[N:1]1([C:7](=[O:9])[CH3:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:10](#[N:13])[CH:11]=[CH2:12]>CO>[C:7]([N:1]1[CH2:6][CH2:5][N:4]([CH2:12][CH2:11][C:10]#[N:13])[CH2:3][CH2:2]1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 837951-Acetylpiperazine

Product 1

HCID 24710353HCID 24710353, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(piperazin-1-yl)ethanone (5 g, 39 mmol) in MeOH (50 mL) at 0° C. is added acrylonitrile (2.57 mL, 39 mmol) in one portion. The resulting reaction is stirred for 12 hours while allowing the reaction to warm to room temperature. 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 6.4 g (91% yield) of the desired compound. 1H NMR (CDCl3, 300 MHz) δ2.08 (s, 3H), 2.46 (t, J=5.1 Hz, 2H), 2.51-2.53 (m, 4H), 2.71 (t, J=6.9 Hz, 2H), 3.48 (t, J=5.1 Hz, 2H), 3.26 (t, J=5.1 Hz, 2H). MS (ESI, pos. ion) m/z: 182 (M+1).

Workup

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

Sources & evidence

ORD record
ord-8b8f35c1eff24a88be0efc4e9abd35fd
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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