1-Phenylpiperazine → 1-Piperazinecarboxamide, N-methyl-N-((methylamino)carbonyl)-4-phenyl-

HRID 979044Notes

Reaction equation

HRID 979044 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][N:14]([C:18]([NH:20][CH3:21])=[O:19])[C:15](Cl)=[O:16]>ClCCl>[CH3:13][N:14]([C:18]([NH:20][CH3:21])=[O:19])[C:15]([N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)=[O:16]

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 122269342,4-Dimethylallophanoyl chloride

Product 1

HCID 30669341-Piperazinecarboxamide, N-methyl-N-((methylamino)carbonyl)-4-phenyl-Yield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 40 ml of dichloromethane, was dissolved 6.5 g of 1-phenylpiperazine. To the solution, while being stirred and cooled in ice, was added dropwise 3.0 g of 2,4-dimethylallophanoyl chloride. After 0.5 hour of reaction at room temperature, the reaction mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was recrystallized from a mixture of ethanol and petroleum ether to obtain 4.0 g (72% yield) of 1-(2,4-dimethyl-allophanoyl)-4-phenylpiperazine having a melting point of 79°-80° C.

Workup

  1. temperaturecooled in ice
  2. customAfter 0.5 hour of reaction at room temperature
  3. washthe reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation
  6. customthe residue was recrystallized from a mixture of ethanol and petroleum ether

Sources & evidence

ORD record
ord-95be9d2502e649edbdb9921d6fe62e13
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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