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Potassium Iodide → HCID 19786565, Verbindung

HRID 1657115
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1657115
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:14](=[O:15])[C:9]2[C:10]([CH3:13])=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:36]=[CH:35][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1.[I-].[K+]>CN(C=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH:5]3[C:14](=[O:15])[C:9]4[C:10]([CH3:13])=[N:11][O:12][C:8]=4[CH2:7][CH2:6]3)[CH2:31][CH2:30]2)=[O:28])=[CH:35][CH:36]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 19786564HCID 19786564, Verbindung

Produkt 1

HCID 19786565HCID 19786565, VerbindungAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution consisting of 5-(3-chloropropyl)-6,7-dihydro-3-methyl-1,2-benzisoxazol-4(5H)-one (0.85 g) and DMF (20 ml) was added anhydrous potassium carbonate (0.52 g) diisopropylethyl amine (0.33 ml), 4-(4-fluorobenzoyl)piperidine (0.92 g) and potassium iodide (62 mg) at room temperature with stirring. The flask was flushed with nitrogen and warmed to 80° C. for 24 hours. Upon cooling to room temperature, water and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with water twice, then brine. The organic phase was then dried (MgSO4), filtered, and concentrated to give the crude product. Purification via flash column chromatography (silica gel, 2% triethylamine/ether) afforded 0.70 g of 6,7-dihydro-5-[3-(4-(4-fluorobenzoyl)-1-piperidinyl)-propyl]-3-methyl -1,2-benzisoxazol-4(5H)-one as an oil which solidified on standing. The product was dissolved and flushed through alumina with dichloromethane. Recrystallization with ether/hexane gave the product as a solid, m.p. 81°-83° C.

Aufarbeitung

  1. customThe flask was flushed with nitrogen
  2. temperatureUpon cooling to room temperature
  3. additionwater and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted 3 times with ethyl acetate
  6. washThe combined organic layers were washed with water twice
  7. dry with materialThe organic phase was then dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product
  11. customPurification via flash column chromatography (silica gel, 2% triethylamine/ether)

Quellen und Nachweise

ORD-Eintrag
ord-c1a8830956cf467cb4ae4089961a665f
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05256672

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