Chloroacetonitrile → 2-(4-Benzylpiperazin-1-yl)acetonitrile

HRID 1162341Notes

Reaction equation

HRID 1162341 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:21][C:22]#[N:23]>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:21][C:22]#[N:23])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 759941-Benzylpiperazine

Product 1

HCID 38557212-(4-Benzylpiperazin-1-yl)acetonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 1-benzylpiperazine (18 g) and sodium carbonate (8.3 g) in acetone (50 ml) was added chloroacetonitrile (12 g) under ice-cooling, and mixed at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, to the residue were added water and diethyl ether, and the organic layer was collected by separation. The organic layer was washed with water and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with silica gel column (ethyl acetate) to obtain the title compound as pale yellow liquid (17 g, 80%).

Workup

  1. temperaturecooling
  2. additionmixed at room temperature for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, to the residue
  4. additionwere added water and diethyl ether
  5. customthe organic layer was collected by separation
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-49746a654edc41f09f637016a9bc8aa1
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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