Morpholine → N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamide

HRID 1095384

Reaktionsgleichung

Reaktionsgleichung von HRID 1095384
Br[CH2:2][C:3]([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:15][CH3:16])=[O:4].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C1COCC1>[CH3:16][O:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 574360272-bromo-N-(2-methoxy-6-nitrophenyl)acetamide

Produkt 1

HCID 57436028N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamideAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-N-(2-methoxy-6-nitrophenyl)acetamide (Step 1, 8.8 g, 30 mmol) in THF (240 mL) was added morpholin (11 mL, 122 mmol) at 0° C. and warmed to rt. After 2.5 h, the reaction mixture was quenched by addition of water (200 mL) and extracted with ethyl acetate (200 mL×2). The combined organic layers were washed with water (200 mL), brine (100 mL) dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1) to afford 6.7 g (75%) of the title compound.

Aufarbeitung

  1. customthe reaction mixture was quenched by addition of water (200 mL)
  2. extractionextracted with ethyl acetate (200 mL×2)
  3. washThe combined organic layers were washed with water (200 mL), brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1)

Quellen und Nachweise

ORD-Eintrag
ord-184fbfc0ca2f49c98231e4027798ca7a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138177B2

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