Water → 3-[3-(3-morpholin-4-yl-3-oxopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-one

HRID 24513Notes

Reaction equation

HRID 24513 reaction equation
[O:1]=[C:2]1[C:10](=[CH:11][C:12]2[NH:13][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[C:20]=2[CH2:21][CH2:22][C:23](O)=[O:24])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.O>CN(C)C=O>[N:38]1([C:23](=[O:24])[CH2:22][CH2:21][C:20]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[NH:13][C:12]=2[CH:11]=[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]2=[O:1])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 541237443-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

Product 1

HCID 571901153-[3-(3-morpholin-4-yl-3-oxopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid (10 g) was dissolved in 100 mL of dimethylformamide. Carbonyldiimidazole (6.3 g) was added and the mixture stirred at ambient temperature for 1 hour. Morpholine (5.2 g) in 30 mL of dimethylformamide was added and the stirring continued overnight. Fifty mL of water was added to the mixture and stirring was continued for 10 minutes. The precipitate was collected by vacuum filtration, washed with 20 mL of water and then 20 mL of ethanol. The solid that formed was slurry-washed with 30 mL of refluxing ethanol for 5 minutes and cooled to room temperature. The solid was collected by vacuum filtration, washed with 20 mL of ethanol and vacuum dried to give 9.6 g (80%) of 3-[3-(3-morpholin-4-yl-3-oxopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-one as an orange solid.

Workup

  1. customthe stirring continued overnight
  2. stirringstirring
  3. waitwas continued for 10 minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with 20 mL of water
  6. customThe solid that formed
  7. washwas slurry-washed with 30 mL of refluxing ethanol for 5 minutes
  8. temperaturecooled to room temperature
  9. filtrationThe solid was collected by vacuum filtration
  10. washwashed with 20 mL of ethanol and vacuum
  11. customdried

Sources & evidence

ORD record
ord-e805cba254cc40debc38f5c9268c5e88
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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