Morpholine → HCID 59441895, compound

HRID 1014323Notes

Reaction equation

HRID 1014323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.C(N(C(C)C)CC)(C)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>ClCCl.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([C:24](=[O:27])[CH2:25][CH2:26][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 8083MorpholineHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441895HCID 59441895, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (1.0 g, 5.15 mmol) and polymer-bound diisopropyl ethylamine (4.20 g, 15.46 mmol) in dichloromethane (200 mL) was added acryloyl chloride (0.51 g, 5.67 mmol) via a dropwise addition. After stirring overnight at rt, the solids were removed by vacuum filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure, and stored under vacuum for several hours. A portion of the crude mixture (0.4 g, 1.61 mmol) was redissolved in absolute ethanol (25 mL) and to this was added morpholine (0.41 g, 4.84 mmol). After heating at 60° C. for 3 hr, the reaction was concentrated under reduced pressure and solids were recrystallized from ethyl acetate/hexanes to provide 5-(methyloxy)-1-[3-(4-morpholinyl)propanoyl]-6-nitro-2,3-dihydro-1H-indole (0.44 g, 54%). ESIMS (M+H)+=336.

Workup

  1. additionvia a dropwise addition
  2. customthe solids were removed by vacuum filtration
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. waitstored under vacuum for several hours
  6. temperatureAfter heating at 60° C. for 3 hr
  7. concentrationthe reaction was concentrated under reduced pressure and solids
  8. customwere recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d68a144e9a48454d9764f9d26da617e7
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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