Sodium Iodide → HCID 19772580, Verbindung

HRID 344684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344684
[CH3:1][O:2][C:3]([C:5]1([N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].Br[CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[OH:25][CH2:24][CH2:23][N:8]1[CH2:9][CH2:10][C:5]([C:3]([O:2][CH3:1])=[O:4])([N:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:6][CH2:7]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 2724431Norcarfentanil

Produkt 1

HCID 19772580HCID 19772580, VerbindungAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (7.34 g, 25 mmol), 2-bromoethanol (3.96 g, 32 mmol), sodium carbonate (20.0 g, 189 mmol), and sodium iodide (1.0 g) in acetonitrile (200ml) was heated to reflux for three days. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum yielding an oily residue. The residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4) to yield 1-(2-hydroxyethyl)-4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (8.1 g, 96%) as an oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for three days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customyielding an oily residue
  7. customThe residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-0a1d0857030e4e41999a13bd5ef55443
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053411

Notizen zur Reaktion

Wird geladen…