Potassium Iodide → 4-Acetyl-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperidine hydrochloride

HRID 280897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280897
[C:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:16][CH2:17][CH2:18][CH2:19][C:20]1[C:24]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=2[O:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:16].[C:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:17][CH2:18][CH2:19][C:20]2[C:24]3[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=3[O:22][N:21]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1015214-Acetyl-4-phenylpiperidineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Produkt 1

HCID 133198744-Acetyl-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperidine hydrochlorideAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 35 ml of dimethylformamide was added 4.06 g of 4-acetyl-4-phenylpiperidine, 5.0 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of milled anhydrous potassium carbonate, and a few crystals of potassium iodide. After stirring at 80° C. for two hrs, the mixture was filtered. The filtrate was evaporated and the residue was stirred with 100 ml of water and then extracted into ether. The ether solution was washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solution was acidified with ethereal hydrogen chloride and the resultant precipitate was collected and dried to yield 5.5 g (66%) of product, mp 170° C. (dec). Three recrystallizations from ethyl acetate:methanol (9:1) gave the analytical sample, mp 200°-203° C.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated
  3. stirringthe residue was stirred with 100 ml of water
  4. extractionextracted into ether
  5. washThe ether solution was washed with water (2x), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customthe resultant precipitate was collected
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6332ce465b774c06a53dba44d46967da
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04591586

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