Potassium Carbonate → HCID 67494052, compound

HRID 1968933Notes

Reaction equation

HRID 1968933 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16]Br)=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:33])[CH:25]=[CH:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:44]3[CH2:45][CH2:46][N:41]([CH3:40])[CH2:42][CH2:43]3)=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:33])[CH:25]=[CH:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67494075HCID 67494075, compound

Product 1

HCID 67494052HCID 67494052, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.4 g of N-(4-methyl-3-(3-(pyridin-3-yl)acrylamido)phenyl)-4-(bromomethyl)-3-(trifluoromethyl)benzamide was added into 20 ml anhydrous tetrahydrofuran, and then 1.0 g of potassium carbonate and 1.0 ml of 4-methyl piperazine. The reaction mixture was heated to reflux for 10 h. The completion of reaction was indicated by TLC. The reaction mixture was filtered, and the filtrate was evaporated to dry. 10 ml of water was added to dissolve the redundant 4-methylpiperazine and corresponding salts. The mixture was filtered, the filter cake was purified on silica gel column using ethyl acetate as an eluent to elute impurities, then using methanol as an eluent to elute the product. Concentration of the eluent under reduced pressure and crystallization gave a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 h
  3. customThe completion of reaction
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated
  6. customto dry
  7. addition10 ml of water was added
  8. dissolutionto dissolve the redundant 4-methylpiperazine and corresponding salts
  9. filtrationThe mixture was filtered
  10. customthe filter cake was purified on silica gel column
  11. washto elute impurities
  12. washusing methanol as an eluent to elute the product
  13. customConcentration of the eluent under reduced pressure and crystallization
  14. customgave a white solid

Sources & evidence

ORD record
ord-0ce5d018527d40a181ad5ca1177ad3f0
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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