Hydrochloric Acid → (4-Fluorophenyl)(piperazin-1-yl)methanone

HRID 1381110Notes

Reaction equation

HRID 1381110 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O>[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)=[O:14])=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 678794-Fluorobenzoyl chlorideHCID 517045Sodium Acetate

Product 1

HCID 771862(4-Fluorophenyl)(piperazin-1-yl)methanoneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Concentrated hydrochloric acid was added dropwise to a solution of piperazine (0.124 mol) in water (110 ml) to adjust the pH to 2.8. The solution was then heated to 50° C. 4-Fluorobenzoyl chloride (0.124 mol) was added to the warm solution dropwise while maintaining the pH at 2.8 by the concurrent addition of 40% aqueous sodium acetate solution. After complete addition, a solution of potassium carbonate (47 g) in water (50 ml) was added and the mixture cooled in an ice bath. The cold mixture was extracted with chloroform (5×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo affording 22.5 g of a white solid (88% yield). Spectral data are consistent with the assigned structure. This material was used without further purification.

Workup

  1. temperaturewhile maintaining the pH at 2.8
  2. additionAfter complete addition
  3. temperaturethe mixture cooled in an ice bath
  4. extractionThe cold mixture was extracted with chloroform (5×150 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9be599ad3d2b4140bc2451d2d3e8332c
Source dataset
uspto-grants-1986_04
Patent number
US04585773

Reaction notes

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