4-Methylmorpholine → 2-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide

HRID 749215

Reaktionsgleichung

Reaktionsgleichung von HRID 749215
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][O:6][C:7]2=[O:12].CN1CCOCC1.[C:20]12([CH2:30][C:31](Cl)=[O:32])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>O1CCOCC1>[C:20]12([CH2:30][C:31]([NH:1][C:2]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][O:6][C:7]4=[O:12])=[O:32])[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]3)[CH2:21]1)[CH2:29]2

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 27718821-Adamantaneacetyl chlorideHCID 100806665-amino-1H-isochromen-1-one

Produkt 1

HCID 597520152-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-amino-1H-isochromen-1-one (2.95 g, 18.3 mmol) and NMM (2.02 mL, 18.3 mmol) in 1,4 dioxane (55 mL) was added dropwise at room temperature a solution of 1-adamantaneacetic acid chloride (3.9 g, 18.3 mmol) in 1,4-dioxane (40 mL). The reaction mixture was stirred at room temperature for 3 h and then partitioned between DCM (400 mL) and water (200 mL). The layers were separated. The aqueous phase was washed with DCM (100 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was suspended in hexane (100 mL) and filtered off. The solid was collected on the filter and dried in vacuo to yield 2-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide as a yellow solid (5.6 g, 16.7 mmol, 91%).

Aufarbeitung

  1. custompartitioned between DCM (400 mL) and water (200 mL)
  2. customThe layers were separated
  3. washThe aqueous phase was washed with DCM (100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. filtrationfiltered off
  8. customThe solid was collected on the
  9. filtrationfilter
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab2f41996fd24e61be44dae0e8627aab
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402596B2

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