Chloroacetonitrile → HCID 20086616, compound

HRID 1608495Notes

Reaction equation

HRID 1608495 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][C:17]#[N:18])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 8518331-(2,3-Dichlorophenyl)piperazine

Product 1

HCID 20086616HCID 20086616, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3-Dichlorophenyl piperazine (5.0 g, 0.0216 mol), chloroacetonitrile (1.37 mL, 0.0216 mol), and potassium carbonate (K2CO3) (14.95 g, 0.108 mol) are combined in acetonitrile and heated to reflux for 18 hours. The reaction mixture is concentrated in vacuo and the resulting residue is partitioned between water (H2O) and dichloromethane. The organic layer is dried (sodium sulfate) and concentrated to give 5.45 g of the title compound as a yellow solid; mp 89°-92° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customthe resulting residue is partitioned between water (H2O) and dichloromethane
  5. dry with materialThe organic layer is dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a063b33ac7c94443a3e22d79122ec36f
Source dataset
uspto-grants-1995_03
Patent number
US05395835

Reaction notes

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