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Diisopropylethylamine → HCID 19786594, Verbindung

HRID 1646736
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1646736
[C:1]1([C:7]2[C:11]3[CH:12]([OH:29])[CH:13]([CH2:16][CH2:17]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:14][CH2:15][C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl.[F:40][C:41]1[CH:54]=[CH:53][C:44]([C:45]([CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)=[O:46])=[CH:43][CH:42]=1>CN(C=O)C>[F:40][C:41]1[CH:42]=[CH:43][C:44]([C:45]([CH:47]2[CH2:52][CH2:51][N:50]([CH2:17][CH2:16][CH:13]3[CH:12]([OH:29])[C:11]4[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[N:8][O:9][C:10]=4[CH2:15][CH2:14]3)[CH2:49][CH2:48]2)=[O:46])=[CH:53][CH:54]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 19786608HCID 19786608, Verbindung

Produkt 1

HCID 19786594HCID 19786594, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution consisting of 3-phenyl-5-(2-tosyloxyethyl)-4-hydroxy-4,5,6,7-tetrahydro-1,2-benzisoxazole (8.0 g) and DMF (100 ml) was added diisopropylethyl amine (6.7 ml) and 4-(4-fluorobenzoyl)piperidine hydrochloride (7.1 g) at room temperature with stirring. The flask was flushed with nitrogen and warmed to 80° C. for 4.5 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 brine and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 2% triethylamine/ether) afforded 1.3 g of 5-[2-(4-(4-fluorobenzoyl)-1-piperidinyl)-ethyl]-3-phenyl-4-hydroxy-4,5,6,7-tetrahydro-1,2-benzisoxazole.

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 brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration
  9. customgave the crude product
  10. customPurification via flash column chromatography (silica gel, 2% triethylamine/ether)

Quellen und Nachweise

ORD-Eintrag
ord-d85208cf43dd4d179b83f9f4640fb2bf
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05180834

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