Potassium Carbonate → HCID 14074120, compound

HRID 621511Notes

Reaction equation

HRID 621511 reaction equation
Br.Br.[OH:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][C:5]=1[CH3:17].Cl[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:3][C:4]1[C:5]([CH3:17])=[CH:6][C:7]([N:11]2[CH2:12][CH2:13][N:14]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)[CH2:15][CH2:16]2)=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 212431721-(4-Hydroxy-3,5-dimethylphenyl)piperazine dihydrobromide

Product 1

HCID 14074120HCID 14074120, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2.21 g (6 mmol) of 1-(4-hydroxy-3,5-dimethylphenyl)piperazine dihydrobromide, 1.14 g (6.25 mmol) of 2-chloro-5-trifluoromethylpyridine and 1.245 g (9 mmol) of K2CO3 in 27 ml of absolute DMF were reacted by the same procedure as described in Example 20. The mixture was subsequently stirred for 3.5 hours at 90° C. After evaporation of the DMF, the residue was mixed with water, and the oily crystalline material produced during this was filtered off under suction, dissolved in methanol and clarified using activated charcoal. After filtration, a little water was added to the filtrate, a crystalline precipitate being produced. This was filtered off under suction (yield 1.63 g) and chromatographed as described in Example 15 on a silica gel/CH2Cl2 column (diameter 2.0 cm, height 22 cm). In this fashion, 1.24 g (=59% yield) of 1-(4-hydroxy-3,5-dimethylphenyl)-4-(5-trifluoromethylpyrid-2-yl)piperazine, melting point 143°-44° C., were obtained;

Workup

  1. customAfter evaporation of the DMF
  2. additionthe residue was mixed with water
  3. customthe oily crystalline material produced during
  4. filtrationthis was filtered off under suction
  5. dissolutiondissolved in methanol
  6. filtrationAfter filtration
  7. additiona little water was added to the filtrate
  8. customa crystalline precipitate being produced
  9. filtrationThis was filtered off under suction (yield 1.63 g)
  10. customchromatographed

Sources & evidence

ORD record
ord-32d7a4b8906a419fb93f0d98f09d1097
Source dataset
uspto-grants-1989_04
Patent number
US04824846

Reaction notes

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