Sodium Iodide → 4-(4-Bromophenylsulphonyl)-1-[2-(2,4-difluorophenyl)ethyl]piperidine

HRID 1836338

Reaktionsgleichung

Reaktionsgleichung von HRID 1836338
[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.[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:21][CH2:20][C:19]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:18]=3[F:17])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27610704-(4-Bromobenzenesulfonyl)piperidineHCID 112989892,4-Difluorophenethyl bromide

Produkt 1

HCID 110485124-(4-Bromophenylsulphonyl)-1-[2-(2,4-difluorophenyl)ethyl]piperidineAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-bromophenylsulphonyl)piperidine (7.6 g, 0.025 mol), 2,4-difluorophenethyl bromide (8.3 g, 0.38 mol), potassium carbonate (7.5 g, 0.054 mol) and sodium iodide (5.6 g, 0.037 mol) in CH3CN (70 ml) was heated at reflux under nitrogen for 18 h. The reaction mixture was then concentrated and partitioned between water and EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Trituration with hexane gave 6.5 g of product as a colourless solid. δH (360 MHz, CDCl3) 1.55-1.75 (2H, m), 1.95-2.05 (4H, m), 2.45-2.55 (2H, m), 2.70-2.75 (2H, m), 2.85-2.95 (1H, m), 3.05-3.10 (2H, m), 6.70-6.85 (2H, m), 7.10-7.15 (1H, m), 7.72 (4H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 18 h
  3. concentrationThe reaction mixture was then concentrated
  4. custompartitioned between water and EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f24e819cbe4249689051c30370095566
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777430B2

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