Potassium Carbonate → 4-(4-Bromophenylsulphonyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]piperidine

HRID 411513

Reaktionsgleichung

Reaktionsgleichung von HRID 411513
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27610704-(4-Bromobenzenesulfonyl)piperidine

Produkt 1

HCID 98894284-(4-Bromophenylsulphonyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]piperidineAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-(4-Bromophenylsulphonyl)piperidine (Example 1 Step d, 0.9 g, 0.003 mol) was added to a mixture of 2-bromo-4′-fluoroacetophenone (0.7 g, 0.0033 mol) and potassium carbonate (0.84 g, 0.006 mol) in acetonitrile (5 ml) and the resulting slurry stirred at room temperature for 17 h. The insolubles were removed by filtration and the solvent evaporated to give a gum which was purified by column chromatography (SiO2, CH2Cl2:MeOH 97:3) to give 0.5 g (36% yield) of product as a colourless solid. δH (400 MHz, CDCl3) 1.75-1.90 (2H, m), 2.05-2.13 (2H, m), 2.25-2.40 (2H, m), 2.85-3.00 (1H, m), 3.04-3.20 (2H, m), 3.75-3.85 (2H, m), 7.12 (1H, t, 8 Hz), 7.24 (4H, s), 7.98-8.02 (2H, m).

Aufarbeitung

  1. customThe insolubles were removed by filtration
  2. customthe solvent evaporated
  3. customto give a gum which
  4. customwas purified by column chromatography (SiO2, CH2Cl2:MeOH 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-afd4547216a94dd6a46cd224acdaf7a0
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559166B1

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