Piperidine → 3-[3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-one

HRID 24511Notes

Reaction equation

HRID 24511 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]=1[CH:15]=O.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][C:19]1=[O:27].N1CCCCC1>C(O)C>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]=1[CH:15]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:18][C:19]1=[O:27]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 112300633-(3-(Dimethylamino)propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Product 1

HCID 498235063-[3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-Dimethylaminopropyl)-2-formyl-4,5,6,7-tetrahydro-1H-indole (1.8 g), 1 g of 2-oxindole and 0.1 g of piperidine in 10 mL of ethanol was refluxed for 4 hours and then cooled to room temperature. The precipitate which formed was collected by vacuum filtration and washed with 4 mL of ethanol. The solids were slurry-washed with 8 mL of refluxing ethanol, cooled, collected by vacuum filtration, washed with 3 mL of ethanol and vacuum dried to give 1.8 g (70% yield) of 3-[3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydroindol-2-one as an orange solid.

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed with 4 mL of ethanol
  4. washThe solids were slurry-washed with 8 mL of refluxing ethanol
  5. temperaturecooled
  6. filtrationcollected by vacuum filtration
  7. washwashed with 3 mL of ethanol and vacuum
  8. customdried

Sources & evidence

ORD record
ord-dbe6373c8ed24e08a754daa965385c11
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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