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

HRID 749215

반응식

HRID 749215 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 597520152-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide수율 91.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ab2f41996fd24e61be44dae0e8627aab
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402596B2

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