Piperidine → 3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 24490Notes

Reaction equation

HRID 24490 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[CH:20]=O.N1CCCCC1>C(O)C>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[CH:20]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96389Indole-2-carboxaldehydeHCID 321710Oxindole

Product 1

HCID 539916113-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-oxindole (133 mg), indole-2-carbaldehyde (174 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (10 mg) in ethanol was held in a sealed tube at 95° C. for 4 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in a vacuum oven to give 3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one.

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. washwashed with cold ethanol
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-184094c529ac45cf94f41c3b3c201982
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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