Phenacyl bromide → (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404680
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N+:14]([CH2:27][C:28](=[O:29])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6259Phenacyl bromideHCID 86688939HCID 86688939, Verbindung

Produkt 1

HCID 86688940(3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(R)-quinuclidin-3-yl 2-(4-chlorophenyl)-2-(piperidin-1-yl)acetate (100 mg, 0.28 mmol) and 2-bromo-1-phenylethanone (60.3 mg, 0.30 mmol) were dissolved in acetonitrile (4 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the resulting residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (98 mg, 63.3% yield) as white powder.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe resulting residue was purified by flash chromatography (DCM/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-9aab93d2271f477c9a6681b00c76579a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748613B2

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