Piperidine → 3-[2-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

HRID 24501Notes

Reaction equation

HRID 24501 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=O.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21]2.N1CCCCC1.N1CCCC1>C(O)C.C(O)(=O)C>[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[C:21]2=[CH:1][C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 31268PyrrolidineHCID 1528015-ChlorooxindoleHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 697634783-[2-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

3-(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5.4 g), 3.7 g of 5-chloro-2-oxindole and 2.7 g of piperidine (or 2.2 g of pyrrolidine) in 25 mL of ethanol was refluxed for 4 hours. Slow addition of acetic acid (8 mL) resulted in a precipitate. The mixture was refluxed for 5 minutes and cooled to ambient temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solids were slurry-washed by refluxing in 30 mL of ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and dried under high vacuum to give 6.5 g (80% yield) 3-[2-(5-chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1-H-indol-3-yl]-propionic acid as an orange solid: mp 370-384° C.

Workup

  1. customresulted in a precipitate
  2. temperatureThe mixture was refluxed for 5 minutes
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with 20 mL of ethanol
  5. washThe solids were slurry-washed
  6. temperatureby refluxing in 30 mL of ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-7430dc6059314ddbaa8d35f8813fd712
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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