Morpholine → (2-Fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanone

HRID 1804682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804682
[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:6]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579556232-Fluoro-3-methoxy-4-nitrobenzoic acid

Produkt 1

HCID 70099135(2-Fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-fluoro-3-methoxy-4-nitrobenzoic acid (180 mg, 0.97 mmol) in DCM (8 mL) was added morpholine (0.17 mL. 1.9 mmol), DIEA (0.25 mL) and HBTU (0.4 g, 1.05 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was then diluted with water and extracted with DCM (3×). The combined extracts were washed with water, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography to give (2-fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanone (0.20 g, 83%).

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-80e43a21bd8d4992bd9178534060ee17
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354420B2

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