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

HRID 1840494Notes

Reaction equation

HRID 1840494 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.[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>[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: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 1528015-Chlorooxindole

Product 1

HCID 542583355-chloro-3-(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), indole-2-carbaldehyde (174 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) 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-(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-c0d18a3d94034513936db3172e09b9bf
Source dataset
uspto-grants-2004_01
Patent number
US06680335B2

Reaction notes

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