Potassium Carbonate → HCID 24206025, compound

HRID 1944989Notes

Reaction equation

HRID 1944989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10]Cl)=[C:4]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>CC(C)=O.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][N:37]2[CH2:38][CH2:39][N:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)[CH2:35][CH2:36]2)=[C:4]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 844102,4'-Dichloro-2'-o-chlorobenzoylacetanilideHCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 24206025HCID 24206025, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a compound of N1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-2-chloroacetamide (500 mg, 1.46 mmol) in dry acetone (20 mL) was added anhydrous potassium carbonate (1 g, 7.30 mmol) and 1-(2-pyridyl)piperazine (238 mg, 1.46 mmol). The reaction mixture was refluxed for 24 h and the reaction was monitored by TLC using ethyl acetate-hexane (6:4) as a solvent system. The potassium carbonate was then removed by suction filtration and the solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product 6a (585 mg, 86% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. customThe potassium carbonate was then removed by suction filtration
  3. customthe solvent was evaporated under vacuum
  4. customto afford the crude product
  5. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-65c3913079284ac69f414a79de9611e8
Source dataset
uspto-grants-2013_03
Patent number
US08394954B2

Reaction notes

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