1-(3-(Trifluoromethyl)phenyl)piperazine → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-trifluoromethylphenyl)piperazine hydrochloride

HRID 64875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64875
[Cl:1][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]([F:30])([F:29])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:26]3[CH2:25][CH2:24][N:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:29])([F:30])[F:15])[CH:18]=4)[CH2:28][CH2:27]3)=[N:6][O:7][C:8]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207371-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-trifluoromethylphenyl)piperazine hydrochlorideAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6.5 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 5.8 g of N-(α,α,α-trifluoro-m-tolyl)piperazine, 7.0 g of potassium carbonate and a few crystals potassium iodide in 80 ml of dimethylformamide was stirred at 70°-75° C. for seven hrs. The reaction mixture was cooled, filtered and concentrated to an oil, which was stirred with water and extracted with ether-ethyl acetate. The organic extracts were washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated to an oil, which was converted to a salt by treatment with ethereal hydrogen chloride. The salt was recrystallized from ethyl acetate/methanol to give 4 g (35%) of product mp, 208°-209° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil, which
  4. extractionextracted with ether-ethyl acetate
  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 to an oil, which
  9. customThe salt was recrystallized from ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-c2676640fd80454395df9609f6d257ce
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610988

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