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

HRID 24500Notes

Reaction equation

HRID 24500 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.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26].N1CCCCC1.N1CCCC1>C(O)C.C(O)(=O)C>[O:26]=[C:18]1[C:19](=[CH:1][C:3]2[NH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[C:11]=2[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:17]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 31268PyrrolidineHCID 321710OxindoleHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 541237443-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 68%

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), 3.6 g of 2-oxindole and 2.7 g of piperidine (or 2.2 g of pyrrolidine) in 25 mL of ethanol were refluxed for 4 hours. Upon slow addition of acetic acid (8 mL), a precipitate formed. 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 refluxing in 30 mL of ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and dried under vacuum to give 5.5 g (68% yield) of 3-[2-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid as an orange solid: mp 263-265° C.

Workup

  1. customa precipitate formed
  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. temperaturerefluxing in 30 mL of ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-829949235fca4b958cf3152d2df3c014
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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