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

HRID 364018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 364018
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.Cl[CH2:18][CH2:19][CH2:20][C:21]1[C:25]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=2[O:23][N:22]=1.[C:31](=[O:34])([O-:33])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[C:5]([OH:4])(=[O:23])[C:31]([OH:33])=[O:34].[F:30][C:28]1[CH:27]=[CH:26][C:25]2[C:21]([CH2:20][CH2:19][CH2:18][N:14]3[CH2:15][CH2:16][N:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=4)[CH2:12][CH2:13]3)=[N:22][O:23][C:24]=2[CH:29]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 814291-(3-Methoxyphenyl)piperazine dihydrochlorideHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207411-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-methoxyphenyl)piperazine oxalateAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 40 ml of dimethylformamide was added 5.3 g of 4-(3-methoxyphenyl)piperazine dihydrochloride, 6.4 g of 3-(3-chloropropvl)-6-fluoro-1,2-benzisoxazole, 10.0 g of milled potassium carbonate, and 0.01 g of potassium iodide. The mixture was stirred at 90° C. for two hrs, cooled, filtered, and evaporated to an oil. The oil was stirred with 100 ml water for ten mins, 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 and the resulting precipitate was collected and dried to give 3.8 g (41%) of product. Two recrystallizations from ethyl acetate/methanol/ether (10:1:5), gave the analytical sample, mp 168° C. (dec).

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated to an oil
  4. stirringThe oil was stirred with 100 ml water for ten mins
  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 resulting precipitate was collected
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-73832ff353cd4089a10218ba81028c19
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604395

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