Potassium Carbonate → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-methoxyphenyl)piperazine oxalate

HRID 64877

Reaktionsgleichung

Reaktionsgleichung von HRID 64877
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.Cl.Cl.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.[C:31](=[O:34])([O-:33])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[C:8]([OH:7])(=[O:18])[C:31]([OH:33])=[O:34].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH2:26][N:25]([C:22]4[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=4)[CH2:30][CH2:29]3)=[N:6][O:7][C:8]=2[CH:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207431-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-methoxyphenyl)piperazine oxalateAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 40 ml of dimethylformamide was added 4.3 g 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 4.0 g of 4-(4-methoxyphenyl)piperazine dihydrochloride, 10.0 g of milled potassium carbonate, and 0.01 g potassium iodide. The mixture was stirred at 90° C. for two hrs, cooled, filtered, and the filtrate evaporated to an oil. The oil was stirred with 100 ml of water and extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, ethereal oxalic acid was added. The precipitate was collected and dried to yield 3.0 g (44%) of product. Two recrystallizations from ethyl acetate/methanol/ether (10:1:5) gave the analytical sample, mp 188°-189° C. (dec).

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to an oil
  4. stirringThe oil was stirred with 100 ml of water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water (2×), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. additionethereal oxalic acid was added
  11. customThe precipitate was collected
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f2823daaa5024119926dc8de134239a6
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610988

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