Piperazine → (2-Fluoro-phenyl)-piperazin-1-yl-methanone

HRID 1032292Notes

Reaction equation

HRID 1032292 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](Cl)=[N:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-:32].[K+].[K+]>ClC(Cl)Cl>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:32].[C:24]1([NH:23][NH2:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 727453432-fluoro-N-phenylbenzenecarbohydrazonoyl chloride

Product 2

HCID 7516PhenylhydrazineHCID 544862(2-Fluoro-phenyl)-piperazin-1-yl-methanoneYield 55.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 12.5 parts of piperazine, 3.6 parts of N,N-diethylethanamine and 75 parts of trichloromethane was added a solution of 9 parts of 2-fluoro-N-phenyl-benzenecarbohydrazonoyl chloride in 75 parts of trichloromethane. The whole was stirred for 2 hours at room temperature. After the addition of 5 parts of potassium carbonate, the reaction mixture was stirred for 30 minutes at reflux temperature. The mixture was cooled, washed with 100 parts of water and the layers were separated. The organic layer was dried, filtered and evaporated, yielding 6 parts (55.8%) of 1-(2-fluorobenzoyl)-piperazine, 2-phenylhydrazine as a residue (int. 9).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. temperatureat reflux temperature
  3. temperatureThe mixture was cooled
  4. washwashed with 100 parts of water
  5. customthe layers were separated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-dd565b7f8f08445dba38c93306b8a538
Source dataset
uspto-grants-1990_09
Patent number
US04957916

Reaction notes

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