Potassium Carbonate → HCID 18423133, compound

HRID 1282072Notes

Reaction equation

HRID 1282072 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 18423133HCID 18423133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an aqueous solution (100 ml) of 1-(4-fluorophenyl)piperazine dihydrochloride was added an aqueous solution (50 ml) of sodium hydroxide (10 g) and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a white solid (ca. 20 g). A solution of this solid (1-(4-fluorophenyl)piperazine), α,α′-dichloro-p-xylene (20.0 g) and potassium carbonate in dimethylformamide (150 ml) was stirred at 75° C. for 2 hr and poured into ice water (500 ml). The mixture was extracted with ethyl acetate (400 ml×2). The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:3) and recrystallized from ethyl acetate-hexane to give the title compound (10.66 g) as white crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (400 ml×2)
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:3)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1bd04392867741ae8809a2c521db7b91
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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