Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

HRID 586517

Reaktionsgleichung

Reaktionsgleichung von HRID 586517
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

7

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridine

Produkt 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholineAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Bromo-2-nitropyridine (5.14 g, 25.3 mmol), tetra-n-butyl ammonium iodide (0.467 g, 1.27 mmol), morpholine (2.43 g, 27.9 mmol) and potassium carbonate (3.85 g, 27.9 mmol) were mixed in DMSO (50 mL). The reaction mixture was warmed to 80° C. for 15 hours. The reaction mixture was diluted with ethyl acetate and the solids removed by filtration. The organic filtrate was washed with water, then the solvent evaporated. The residue was then triturated with a dichloromethane/hexanes mixture to provide 4-(6-nitro-pyridin-3-yl)-morpholine as brown needles (2.90 g, 54.8%). 1H NMR δ (400 MHz, CDCl3) 8.16 (m, 1H), 7.97 (d, J=2.9 Hz, 1H), 7.15 (dd, J=3.2, 9.3 Hz, 1H), 3.45 (m, 4H), 1.72 (m, 4H).

Aufarbeitung

  1. customthe solids removed by filtration
  2. washThe organic filtrate was washed with water
  3. customthe solvent evaporated
  4. customThe residue was then triturated with a dichloromethane/hexanes mixture

Quellen und Nachweise

ORD-Eintrag
ord-37fe36c73def478fa5119c4c399ed3e8
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936612B2

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