Toluene → HCID 15712538, compound

HRID 1088690Notes

Reaction equation

HRID 1088690 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[N:13]2[CH:27]=[N:28][C:29]([C:30]#[N:31])=[C:12]12)=[O:10].[C:32](=O)([O-])[O-:33].[Na+].[Na+].[OH-].[Na+].[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CCOCC>[CH3:32][O:33][C:42]1[CH:41]=[C:40]([CH2:46][N:1]2[CH2:6][CH2:5][N:4]([CH2:8][C:9]([N:11]3[CH2:16][CH:15]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[N:13]4[CH:27]=[N:28][C:29]([C:30]#[N:31])=[C:12]34)=[O:10])[CH2:3][CH2:2]2)[CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 4837PiperazineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 15712537HCID 15712537, compound

Product 1

HCID 15712538HCID 15712538, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 800 mg of 1-[3-methoxyphenyl)methyl]piperazine, 1.2 g of 1-(chloroacetyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile and 450 mg of sodium carbonate in 50 ml of toluene was heated at reflux for 18 hours, then allowed to stand at room temperature. The mixture was treated with 10 ml of 1N sodium hydroxide and the phases were separated. The aqueous phase was extracted twice with chloroform. The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a viscous oil. The oil was treated with 15 ml of ether and scratching to separate tan crystals. The crystals were collected, washed with ether and dried. The dried material was dissolved in 15 ml of ethyl acetate with heating, then the solution was filtered. The filtrate was mixed with 30 ml of n-hexane and stored in a refrigerator until crystals formed. The product was collected by filtration, pressed to remove solvent then washed with hexane and dried in vacuo to give 1.25 g of the desired product, mp 131°-133° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customto stand at room temperature
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted twice with chloroform
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain a viscous oil
  11. customto separate tan crystals
  12. customThe crystals were collected
  13. washwashed with ether
  14. customdried
  15. dissolutionThe dried material was dissolved in 15 ml of ethyl acetate
  16. temperaturewith heating
  17. filtrationthe solution was filtered
  18. additionThe filtrate was mixed with 30 ml of n-hexane
  19. customformed
  20. filtrationThe product was collected by filtration
  21. customto remove solvent
  22. washthen washed with hexane
  23. customdried in vacuo

Sources & evidence

ORD record
ord-2b2ced7973b94ccdbbafaa808a7f9673
Source dataset
uspto-grants-1990_10
Patent number
US04963552

Reaction notes

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