Piperidine → ethyl (E)-3-[(2-oxo-1,2-dihydroindol-3-ylidenemethyl)phenyl]propionate

HRID 24530Notes

Reaction equation

HRID 24530 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=O.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C:17]1=[O:25].N1CCCCC1>C(O)C>[O:25]=[C:17]1[NH:16][C:24]2[C:19](/[C:18]/1=[CH:1]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:20][CH:21]=[CH:22][CH:23]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 53401261Ethyl 3-(2-formylphenyl)prop-2-enoate

Product 1

HCID 86591008ethyl (E)-3-[(2-oxo-1,2-dihydroindol-3-ylidenemethyl)phenyl]propionateYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1 g of ethyl 3-(2-formylphenyl)propenate, 500 mg oxindole and 0.1 mL piperidine in 5 mL of ethanol was stirred at 90° C. overnight. The mixture was evaporated and purified on a silica gel column to give 450 mg of ethyl (E)-3-[(2-oxo-1,2-dihydroindol-3-ylidenemethyl)phenyl]propionate (M+1=322).

Workup

  1. customThe mixture was evaporated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-15c001fb00a64568a6ec8ef3bf9b38a8
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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