Iodoacetamide → 2-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide

HRID 1262387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262387
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.I[CH2:18][C:19]([NH2:21])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:18][C:19]([NH2:21])=[O:20])[CH2:13][CH2:12]1

Komponenten

6

Edukt 4

HCID 3727IodoacetamideHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 27830661-(2-fluoro-4-nitrophenyl)piperazine

Produkt 1

HCID 471845052-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamideAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-(2-Fluoro-4-nitro-phenyl)-piperazine (0.438 g, 1.94 mmol), Iodoacetamide (0.401 g, 2.17 mmol), Cesium Carbonate (0.956 g, 2.93 mmol) and Acetonitrile (20 mL, 400 mmol) were combined and stirred at 60° C. for 20 hours. The mixture was cooled to room temperature. Water was added to the mixture and the product was extracted into ethyl acetate three times. The extracts were dried over sodium sulfate, filtered and concentrated to yield a yellow solid, 2-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide (558 mg, 100%). LCMS: m/z=283.06 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 8.00 (d, 2H), 7.26 (br s, 1H), 7.17 (m, 2H), 2.94 (s, 2H), 2.60 (m, 2H), 2.50 (s, 6H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe product was extracted into ethyl acetate three times
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ebcd69378d2643caa0fda3fdbb80ac59
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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