Chloroacetonitrile → (4-Acetylpiperazin-1-yl)acetonitrile

HRID 1351411Notes

Reaction equation

HRID 1351411 reaction equation
Cl[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[Na+].[Na+].[C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])[CH3:12]>C1(C)C=CC=CC=1>[C:11]([N:14]1[CH2:19][CH2:18][N:17]([CH2:2][C:3]#[N:4])[CH2:16][CH2:15]1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 837951-Acetylpiperazine

Product 1

HCID 21098286(4-Acetylpiperazin-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chloroacetonitrile (14.7 ml, 234 mmol) was added slowly to a well stirred suspension of sodium carbonate (32 g, 300 mmol) and acetylpiperazine (30 g, 230 mmol) in toluene (200 ml). The mixture was heated under reflux for 3 hours. The reaction was cooled, filtered and the filtrate evaporated under reduced pressure. The resulting solid was recrystallised from ethyl acetate to afford the title compound as a yellow solid, 18.6 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customThe resulting solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-bebc8e36332e404088ad90705d9c0040
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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