Methyl Isocyanate → 1-Piperazinecarboxamide, N-methyl-N-((methylamino)carbonyl)-4-(3-(trifluoromethyl)phenyl)-

HRID 979047Notes

Reaction equation

HRID 979047 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:21][N:22]=[C:23]=[O:24]>ClCCl>[CH3:1][N:2]([C:23]([NH:22][CH3:21])=[O:24])[C:3]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 20201640HCID 20201640, compound

Product 1

HCID 30669401-Piperazinecarboxamide, N-methyl-N-((methylamino)carbonyl)-4-(3-(trifluoromethyl)phenyl)-Yield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 70 ml of dichloromethane, was dissolved 4.3 g of 1-(methylcarbamoyl)-4-(m-trifluoromethylphenyl)piperazine and 0.9 g of methyl isocyanate. To the solution, while being stirred and cooled in ice, was added dropwise 3.9 g of anhydrous stannic chloride. After 15 hours of reaction at room temperature, the precipitated matter was collected by filtration and stirred in a mixture of dichloromethane and water. The organic layer was separated and dried over anhydrous sodium sulfate. After removal of the solvent by distillation, the residue was recrystallized from a mixture of ethanol and petroleum ether to obtain 3.2 g (62% yield) of 1-(2,4-dimethylallophanoyl)-4-(m-trifluoromethylphenyl)piperazine.

Workup

  1. temperaturecooled in ice
  2. customAfter 15 hours of reaction at room temperature
  3. filtrationthe precipitated matter was collected by filtration
  4. stirringstirred in a mixture of dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. distillationby distillation
  9. customthe residue was recrystallized from a mixture of ethanol and petroleum ether

Sources & evidence

ORD record
ord-01899a6e3fc54fca9bdbf621faf6ec7e
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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