Piperidine → 5-bromo-3-(1H-indol-2-ylmethylene)-1,3-dihydroindol-2-one

HRID 24492Notes

Reaction equation

HRID 24492 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH:21]=O.N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:21][C:13]1[NH:12][C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96389Indole-2-carboxaldehydeHCID 6111935-Bromo-2-oxindole

Product 1

HCID 542680455-bromo-3-(1H-indol-2-ylmethylene)-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-2-oxindole (212 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 5-bromo-3-(1H-indol-2-ylmethylene)-1,3-dihydroindol-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-5248c7e7e0b046bd8a8ebef9d912684b
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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