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Potassium Iodide → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-methylpiperazine dihydrochloride

HRID 364022
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 364022
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][CH2:9][CH2:10][CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=2[O:14][N:13]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:8].[ClH:8].[F:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[N:13][O:14][C:15]=2[CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207491-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-methylpiperazine dihydrochlorideAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 30 ml of dry dimethylformamide was added 2.0 g of 4-methylpiperazine, 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate and a few crystals of potassium iodide. After stirring at 100° C. for one and one-half hrs, the mixture was filtered. The filtrate was evaporated to an oil. The oil was stirred with 100 ml water for five mins and extracted with ether. The ether solution was washed with water (2×), saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to an oil, which was dissolved in ether and converted to a salt by treatment with ethereal hydrogen chloride. Recrystallization from ethyl acetate/methanol/ether gave 3.2 g (46%) of product, mp 240° C. (dec). Recrystallization from ethyl acetate/methanol/ether gave the analytical sample, mp 245° (dec).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml water for five mins
  4. extractionextracted with ether
  5. washThe ether solution was washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated to an oil, which
  9. dissolutionwas dissolved in ether
  10. customRecrystallization from ethyl acetate/methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-555b188d10834e519539fe995b866d62
Quelldatensatz
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04604395

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