Benzoyl chloride → HCID 14909614, compound

HRID 1157322Notes

Reaction equation

HRID 1157322 reaction equation
[C:1]1([C:7]2[C:8]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:9][C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:26]([N:17]1[CH2:18][CH2:19][N:14]([C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][NH:11][C:10](=[O:13])[CH:9]=2)[CH2:15][CH2:16]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 27679166-Phenyl-5-(piperazin-1-yl)pyridazin-3(2H)-one

Product 1

HCID 14909614HCID 14909614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 ml three necked round bottom flask was charged with 6-phenyl-5-(piperazin-1-yl)pyridazin-3(2H)-one (2.0 g), dry potassium carbonate (2.1 g) and dry DMF (150 ml) under nitrogen atmosphere. The reaction mixture was stirred at room temperature and benzoylchloride (1.5 g) was added into the reaction mixture very slowly. The reaction mixture was heated 120° C. for 4 hrs. The progress of reaction was monitored by TLC. After consumption of starting material reaction mixture was cooled to 0° C., ice-cold water (20.0 ml) was added to reaction mixture and the organic compound was extracted into ethylacetate (4×20 ml). Combined organic layers were dried (Na2SO4) and concentrated. The crude material was purified by column chromatography using MeOH/CHCl3 (1:9) as eluent to afford 5-(4-benzoylpiperazin-1-yl)-6-phenylpyridazin-3 (2H)-one.

Workup

  1. temperatureThe reaction mixture was heated 120° C. for 4 hrs
  2. customThe progress of reaction
  3. customAfter consumption of starting material reaction mixture
  4. temperaturewas cooled to 0° C.
  5. additionice-cold water (20.0 ml) was added to reaction mixture
  6. extractionthe organic compound was extracted into ethylacetate (4×20 ml)
  7. dry with materialCombined organic layers were dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-622c4b31c51e4e709667acf3c7288287
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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