Water → HCID 90408625, Verbindung

HRID 594075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594075
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10](Cl)[CH:9]=1.[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Br:7][C:8]1[CH:13]=[C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:11]=[C:10]([N:1]2[CH2:6][CH2:16][O:19][CH2:3][CH2:2]2)[CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 10796Cesium carbonateHCID 202807664-Bromo-2,6-dichloropyridine

Produkt 1

HCID 90408625HCID 90408625, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of Morpholine (5.0 equiv.) and 4-bromo-2,6-dichloropyridine (1.0 equiv.) in DMF (0.275 M) was added cesium carbonate (2.0 equiv.). The mixture was heated at 100° C. for 45 hours. LCMS analysis indicated formation of several products including the desired (M+H=288, Rt=0.87 min). The reaction mixture was then concentrated in vacuo to yield a glassy foam. Water was then added, and the mixture was extracted with ethyl acetate, and the combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed via ISCO to provide 4,4′-(4-bromopyridine-2,6-diyl)dimorpholine (44%, 80% purity by LC) as a white crystalline solid. LCMS (m/z) (M+H)=288.0, Rt=0.87 min

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto yield a glassy foam
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed via ISCO

Quellen und Nachweise

ORD-Eintrag
ord-27628f031e8346c08886251fb42fdf15
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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