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Piperidine → 3-[5-(2-Dimethylamino-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one

HRID 1790920
Notes
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Reaction equation

HRID 1790920 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].[CH3:11][N:12]([CH3:27])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH:25]=O)=[CH:19]2.N1CCCCC1>C(O)C>[CH3:11][N:12]([CH3:27])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH:25]=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])=[CH:19]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 220421415-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde

Product 1

HCID 695866633-[5-(2-Dimethylamino-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-oneYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of oxindole (28 mg, 0.216 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 59 mg (79%) of the title compound as an orange solid.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-5613d7906dbc41708c93702a7c443c0b
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071332B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes