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

HRID 979046Notes

Reaction equation

HRID 979046 reaction equation
ClCCl.[C:4]1([N:10]2[CH2:15][CH2:14][N:13]([C:16]([NH2:18])=[O:17])[CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:19][N:20]=[C:21]=[O:22]>O>[CH3:19][NH:20][C:21](=[O:22])[NH:18][C:16]([N:13]1[CH2:12][CH2:11][N:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:15][CH2:14]1)=[O:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 2503654-Phenylpiperazine-1-carboximidic acid

Product 1

HCID 30669291-Piperazinecarboxamide, N-((methylamino)carbonyl)-4-phenyl-Yield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 70 ml of dichloromethane, were dissolved 4.1 g of 4-phenylpiperazine-1-carboxamide and 1.2 g of methyl isocyanate. To the solution, while being stirred and cooled in ice, was added dropwise 5.2 g of stannic chloride. After 15 hours of reaction at room temperature, water was added to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate and freed from the solvent by distillation. The residue was recrystallized from ethanol to obtain 2.7 g (51% yield) of 1-(4-methylallophanoyl)-4-phenylpiperazine having a melting point of 198°-200° C.

Workup

  1. temperaturecooled in ice
  2. customAfter 15 hours of reaction at room temperature
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationfreed from the solvent by distillation
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2fd9087da28744bb97d7896d2407f40e
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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