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

HRID 1840500Notes

Reaction equation

HRID 1840500 reaction equation
[Cl: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.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH:22]=O.N1CCCCC1>C(O)C>[Cl: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:22][C:14]1[NH:15][C:16]2[C:21]([C:13]=1[CH3:12])=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1528015-ChlorooxindoleHCID 2772603-Methyl-1H-indole-2-carbaldehyde

Product 1

HCID 542795775-chloro-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-chloro-2-oxindole (167 mg), 3-methyl-indole-2-carbaldehyde (190 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (10 mg) in ethanol was heated 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 vacuum oven for overnight to give 5-chloro-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with cold ethanol
  4. customdried in vacuum oven for overnight

Sources & evidence

ORD record
ord-c5e16205329a4b248cc3ea511d9914cd
Source dataset
uspto-grants-2004_01
Patent number
US06680335B2

Reaction notes

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