Acetyl chloride → 1-Acetyl-4-(4-nitrophenyl)piperazine

HRID 1826589Notes

Reaction equation

HRID 1826589 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:25](=[O:27])[CH3:26])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 804471-(4-Nitrophenyl)piperazineHCID 81531Diisopropylethylamine

Product 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g (24.1 mmol) of 1-(4-nitro-phenyl)-piperazine in 100 mL of dichloromethane was added 5.04 mL (28.9 mmol) of diisopropyl-ethylamine. The solution is cooled in an ice-bath, treated with 1.89 mL (26.5 mmol) of acetyl chloride, and stirred at room temperature overnight. The reaction is washed successively with water, 0.5 M HCl, saturated sodium hydrogen carbonate, and brine, and dried over magnesium sulfate, and concentrated to give 5.91 g (98.5%) of the product as a solid.

Workup

  1. temperatureThe solution is cooled in an ice-bath
  2. washThe reaction is washed successively with water, 0.5 M HCl, saturated sodium hydrogen carbonate, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9dae745ed9fe40cba728f17dfedf5a55
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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