Oxalic Acid → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-fluorophenyl)piperazine oxalate

HRID 64614

Reaktionsgleichung

Reaktionsgleichung von HRID 64614
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>CN(C)C=O>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)=[N:6][O:7][C:8]=2[CH:13]=1

Komponenten

7

Edukt 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207331-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-fluorophenyl)piperazine oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 4.0 g of 1-(4-fluorophenyl)piperazine, 10 g of potassium carbonate and a few crystals potassium iodide in 70 ml of dimethylformamide was stirred at 80° C. for 4.5 hr. The mixture was cooled, filtered and concentrated to an oil, which was stirred with water and extracted with ethyl acetate-ether. The organic extracts were washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated. The residue was purified by column chromatography (silica gel, tetrahydrofuran) to give an oil. The oil was converted to 4.5 g (45%) of product by treatment with oxalic acid. Two recrystallizations from ethyl acetate/methanol gave the analytical sample, mp 186°-187° C. (dec).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil, which
  4. extractionextracted with ethyl acetate-ether
  5. washThe organic extracts were washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, tetrahydrofuran)
  10. customto give an oil
  11. customTwo recrystallizations from ethyl acetate/methanol
  12. customgave the analytical sample, mp 186°-187° C. (dec)

Quellen und Nachweise

ORD-Eintrag
ord-ec7fb6350741470a988d0e5ad0be3d81
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609658

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