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Ethyl Acetate → HCID 19786595, Verbindung

HRID 1646743
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1646743
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[C:21](=[O:22])[C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:12][O:13][C:9]=2[CH2:8][CH2:7]1)[CH3:4].Cl.[F:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([CH:31]2[CH2:36]CNC[CH2:32]2)=[O:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[F:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([CH:31]2[CH2:32][CH2:2][N:3]([CH2:5][CH:6]3[C:21](=[O:22])[C:10]4[C:11]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=5[F:20])=[N:12][O:13][C:9]=4[CH2:8][CH2:7]3)[CH2:4][CH2:36]2)=[O:30])=[CH:37][CH:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 19786590HCID 19786590, Verbindung

Produkt 1

HCID 19786595HCID 19786595, VerbindungAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a solution consisting of 6,7-dihydro-5-dimethylaminomethyl-3-(2-fluorophenyl)-1,2-benzisoxazol-4(5H)-one hydrochloride (1.86 g) in distilled water (18.5 ml) was added 4-(4-fluorobenzoyl)piperidine hydrochloride (2.78 g) and potassium carbonate (0.80 g). The reaction mixture was heated at reflux for 3 hours. Upon cooling to room temperature, ethyl acetate was added and the layers were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 40% ethyl acetate/hexane) afforded 1.20 g of 6,7-dihydro-5-(4-(4-fluorobenzoyl)-1-piperidinyl)methyl-3-(2-fluorophenyl)-1,2-benzisoxazol-4(5H)-one. The compound was flushed through alumina with dichloromethane to give an oil which solidified on standing. The product was then recrystallized from ether/hexane, m.p. 99°-102° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration
  8. customgave the crude product
  9. customPurification via flash column chromatography (silica gel, 40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f7f280b3f707439e80035aa51b234ec9
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05180834

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