Morpholine → 3-Cyano-5-(4-fluorophenyl)-4-methyl-2-morpholinopyrrole

HRID 610041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610041
[C:1]([CH2:3][C:4](=[NH:8])OCC)#[N:2].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(=O)([O-])O.[Na+].Br[CH:21]([CH3:31])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=O>C(O)C.NC(N1CCOCC1)=CC#N>[C:1]([C:3]1[C:21]([CH3:31])=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[NH:8][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)#[N:2]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 256188Ethyl 2-cyanoethanecarboximidateHCID 516892Sodium BicarbonateHCID 130516522-Bromo-1-(4-fluorophenyl)propan-1-one

Produkt 1

HCID 158712973-Cyano-5-(4-fluorophenyl)-4-methyl-2-morpholinopyrroleAusbeute 4,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 27636313-Amino-3-morpholinoacrylonitrileLösungsmittel

Versuchsvorschrift

In anhydrous ethanol (10 ml) was dissolved 3-amino-3-morpholinoacrylonitrile, as prepared from ethyl 2-cyano-acetimidate (1.0 g) and morpholine (0.78 g) as in Reference Example 3, followed by addition of sodium hydrogen carbonate (0.95 g). Then, a solution of 2-bromo-4'-fluoropropiophenone (2.06 g) in ethanol was added dropwise thereto at room temperature with stirring. The mixture was refluxed for 10 minutes and, then, stirred at room temperature overnight. The separated crystal crop was collected by filtration and recrystallized from ethanol to provide the title compound as colorless crystals (0.12 g). m.p. 245-247° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 10 minutes
  2. stirringstirred at room temperature overnight
  3. filtrationThe separated crystal crop was collected by filtration
  4. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-26083fae6cec4dfd85d3186086ac8543
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998459

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