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Sodium Iodide → HCID 19786559, Verbindung

HRID 1646725
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1646725
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([OH:43])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1.[I-].[Na+]>CN(C=O)C>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([OH:43])[CH2:38][CH2:39][N:40]([CH2:2][CH2:3][CH2:4][CH:5]3[C:19](=[O:20])[C:9]4[C:10]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)=[N:11][O:12][C:8]=4[CH2:7][CH2:6]3)[CH2:41][CH2:42]2)=[CH:33][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 81531DiisopropylethylamineHCID 19786584HCID 19786584, Verbindung

Produkt 1

HCID 19786559HCID 19786559, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution consisting of 5-(3-chloropropyl)-6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one (5.02 g) and DMF (170 ml) was added diisopropylethyl amine (7.50 ml), 4-(4-chlorophenyl)-4-hydroxypiperidine (4.03 g) and sodium iodide (2.59 g) at room temperature with stirring. The reaction was flushed with nitrogen and warmed to 78°-80° C. for 11 hours. Upon cooling to room temperature, water and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous layers extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude amine product. Purification via flash chromatography (silica gel, 2% Et3N/ether) afforded 2.60 g of the desired product as an oil. Addition of ether, heat, and slow evaporation gave a powder. The ether was then decanted and the powder was washed with pentane to yield 5-[3-(4-(4-chlorophenyl)-4-hydroxy-piperidinyl)-propyl]-6,7-dihydro-3-phenyl-1,2-benzisoxazol- 4(5H)-one, m.p. 147°-148° C.

Aufarbeitung

  1. customThe reaction was flushed with nitrogen
  2. temperaturewarmed to 78°-80° C. for 11 hours
  3. additionwater and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous layers extracted three 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 amine product
  10. customPurification via flash chromatography (silica gel, 2% Et3N/ether)

Quellen und Nachweise

ORD-Eintrag
ord-ccd296f185e7465998d00a554a276275
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05180834

Notizen zur Reaktion

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