Potassium Carbonate → HCID 24206026, compound

HRID 1944990Notes

Reaction equation

HRID 1944990 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]=[N: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[N:28]=[CH:33][CH:32]=[CH:31][N:30]=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 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 24206026HCID 24206026, compoundYield 83.7%

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-pyrimidinyl)piperazine (239 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 6b (575 mg, 83% 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-105a4f962699478ebf480ca6f5ed2088
Source dataset
uspto-grants-2013_03
Patent number
US08394954B2

Reaction notes

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