Potassium Carbonate → 4-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidine

HRID 914996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914996
CS(O[CH2:6][CH2:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)(=[O:10])=[O:9])(=O)=O.[CH2:20]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:6][CH2:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)(=[O:10])=[O:9])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 589580692-(3-Nitro-benzenesulfonyl)ethyl methanesulfonate

Produkt 1

HCID 589580954-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 102 (1.0 g, 3.2 mmol), 4-benzylpiperidine (103) (0.62 g, 3.5 mmol), and potassium carbonate (1.1 g, 8.0 mmol) in acetonitrile (10 ml) was heated at 70° C. overnight. It was allowed to cool to room temperature and partitioned between EtOAc (150 mL) and water (150 mL). The organic layer was washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc) to give 104 (0.26 g, 21%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (150 mL) and water (150 mL)
  3. washThe organic layer was washed with water (100 ml), brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-fe2f3574e2734c1f980f4c895d8bb1a7
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265122B2

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