Piperidine → 5-acetyl-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 24485

Reaction equation

HRID 24485 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)(=[O:3])[CH3:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH:23]=O.N1CCCCC1>C(O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[CH:23][C:15]1[NH:14][C:22]2[C:17]([CH:16]=1)=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96389Indole-2-carboxaldehydeHCID 102196435-acetyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 543587105-acetyl-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-acetyl-2-oxindole (88 mg), indole-2-carbaldehyde (87 mg) and piperidine (4 mg) in ethanol (2 mL) was held in a sealed tube at 90° C. for 3 hours. The mixture was cooled to room temperature. The solid which formed was collected by vacuum filtration, washed with cold ethanol and dried in a vacuum oven to give 133 mg (88% yield) of 5-acetyl-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one as an orange solid.

Workup

  1. customThe solid which formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed with cold ethanol
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-74f8a3e33b3a42748db59d30cf18d457
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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