Potassium Carbonate → HCID 9279493, compound

HRID 621510Notes

Reaction equation

HRID 621510 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Product 1

HCID 9279493HCID 9279493, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6.82 g (20 mmol) of 1-(4-hydroxyphenyl)piperazine dihydrobromide, 3.36 g (18.5 mmol) of 2-chloro-5-trifluoromethylpyridine, 2.91 g (21 mmol) of powdered K2CO3 and 76 ml of absolute DMF was warmed to 80° C., and 460 mg of powdered K2CO3 were added with stirring at 80° C. in each case after 10 minutes, after a further 25 minutes and after a further 60 minutes (a total of 1.38 g (10 mmol) of K2CO3), and the mixture was stirred for a further 9 hours at 80° C. After removing the DMF by distillation in vacuo, the residue was taken up in CH2Cl2 /water, the phases were separated after thorough mixing, and the aqueous solution was extracted three times with CH2Cl2. The combined CH2Cl2 extracts were dried, filtered and evaporated in vacuo. The residue (6 g) was dissolved in boiling methanol. The turbid solution formed was filtered through kieselguhr under suction, concentrated to half the volume, and cooled in an ice bath. The crystals which precipitated out were filtered off under suction and dried. The filtrate, after further concentration and cooling, precipitated further crystalline substance, which was filtered off under suction and recrystallized from a little methanol. In this fashion, 3.43 g (=57.4% yield) of 1-(4-hydroxyphenyl)-4-(5-trifluoromethylpyrid-2-yl)piperazine, melting point 178°-79° C., were obtained.

Workup

  1. customAfter removing the DMF
  2. distillationby distillation in vacuo
  3. customthe phases were separated after thorough mixing
  4. extractionthe aqueous solution was extracted three times with CH2Cl2
  5. dry with materialThe combined CH2Cl2 extracts were dried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. dissolutionThe residue (6 g) was dissolved
  9. customThe turbid solution formed
  10. filtrationwas filtered through kieselguhr under suction
  11. concentrationconcentrated to half the volume
  12. temperaturecooled in an ice bath
  13. customThe crystals which precipitated out
  14. filtrationwere filtered off under suction
  15. customdried
  16. concentrationThe filtrate, after further concentration
  17. temperaturecooling
  18. customprecipitated further crystalline substance, which
  19. filtrationwas filtered off under suction
  20. customrecrystallized from a little methanol

Sources & evidence

ORD record
ord-f80c26b1b06d4158aca8035b7f366933
Source dataset
uspto-grants-1989_04
Patent number
US04824846

Reaction notes

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