1-(2-Hydroxyethyl)piperazine → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(2-hydroxyethyl)piperazine dihydrochloride

HRID 64878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64878
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[Cl:10][CH2:11][CH2:12][CH2:13][C:14]1[C:18]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=2[O:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[ClH:10].[ClH:10].[F:23][C:21]1[CH:20]=[CH:19][C:18]2[C:14]([CH2:13][CH2:12][CH2:11][N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]3)=[N:15][O:16][C:17]=2[CH:22]=1

Komponenten

6

Edukt 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 135207451-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(2-hydroxyethyl)piperazine dihydrochlorideAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 50 ml of dimethylformamide was added 2.6 g of 4-(2-hydroxyethyl)piperazine, 6.4 g of 3-(3-chloropropyl)-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 five 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 hydrogen chloride was added, and the precipitate was collected and dried to give 4.3 g (57%) of product. Two recrystallizations from ethyl acetate/methanol, gave the analytical sample, mp 228° 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 hydrogen chloride was added
  11. customthe precipitate was collected
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-43379c75104b4fb3a70a9def57098dd5
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610988

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