Dichloromethane → 1-Piperazinecarboxamide, N-((dimethylamino)carbonyl)-4-(4-fluorophenyl)-N-methyl-

HRID 979045Notes

Reaction equation

HRID 979045 reaction equation
ClCCl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[CH3:17][N:18]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:19](Cl)=[O:20]>C(N(CC)CC)C>[F:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:19](=[O:20])[N:18]([CH3:17])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 752601-(4-Fluorophenyl)piperazineHCID 11062732HCID 11062732, compound

Product 1

HCID 30669481-Piperazinecarboxamide, N-((dimethylamino)carbonyl)-4-(4-fluorophenyl)-N-methyl-Yield 74.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 80 ml of dichloromethane, were dissolved 10.8 g of 1-(p-fluorophenyl)piperazine and 6.1 g of triethylamine. To the solution, while being stirred and cooled in ice, was added dropwise 10.0 g of 2,4,4-trimethylallophanoyl chloride. After one 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 ether to obtain 13.7 g (74% yield) of 1-(p-fluorophenyl)-4-(2,4,4-trimethylallophanoyl)piperazine having a melting point of 83°-84° C.

Workup

  1. temperaturecooled in ice
  2. customAfter one 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 ether

Sources & evidence

ORD record
ord-4f3067b1ab0d429693e20d0fa6ed1e5d
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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