Morpholine → HCID 28491368, Verbindung

HRID 457323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457323
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CC(N(C)C)=O>[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8083Morpholine2×HCID 15553Clopyralid

Produkt 1

HCID 28491368HCID 28491368, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3,6 Dichloropyridine-2-carboxylic acid (0.55 g, 2.86 mmol), morpholine (1.37 g, 15.7 mmol) and N,N dimethylacetamide (1.37 mL) were combined and stirred for 24 h at 80° C. An additional volume of morpholine (1.39 g, 15.7 mmol) was added and heating continued for 40 hours more. After cooling the DMA was removed in the presence of toluene. The residue was dissolved in water and extracted with ether to remove excess morpholine. The aqueous was acidified to pH=2 and the product extracted into ether. Crystallization from water gave a white solid, 369 mg (53% yield). 1H NMR (CD3OD): δ 3.52 (t, 4H), 3.78 (t, 4H), 6.97 (d,1H), 7.65 (d, 1H). LC-MS, M+H: 243.

Aufarbeitung

  1. temperatureheating
  2. waitcontinued for 40 hours
  3. customwas removed in the presence of toluene
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether
  6. customto remove excess morpholine
  7. extractionthe product extracted into ether
  8. customCrystallization from water
  9. customgave a white solid, 369 mg (53% yield)

Quellen und Nachweise

ORD-Eintrag
ord-21309f66d5aa47e88548da64576b0835
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186743B2

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