Piperidine → 2-Methyl-6-[2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid ethyl ester

HRID 2213560Notes

Reaction equation

HRID 2213560 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].[CH2:11]([O:13][C:14]([C:16]1[C:17]2[CH2:24][CH2:23][C:22](=O)[C:18]=2[NH:19][C:20]=1[CH3:21])=[O:15])[CH3:12].N1CCCCC1>CN(C=O)C>[CH2:11]([O:13][C:14]([C:16]1[C:17]2[CH2:24][CH2:23]/[C:22](=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)/[C:18]=2[NH:19][C:20]=1[CH3:21])=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 21051547HCID 21051547, compound

Product 1

HCID 113706862-Methyl-6-[2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid ethyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of oxindole (44 mg, 0.33 mmol) and 2-methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid ethyl ester (Example A, 62 mg, 0.3 mmol) in DMF (5 mL)-piperidine (0.5 mL) was heated at 110° C. with stirring for 72 hours. Most of the solvent was removed under reduced pressure and the residue was diluted with ethanol. The resulted precipitate was collected by filtration, washed with ethanol and dried to give 56 mg (58%) of the titled compound as a yellow solid.

Workup

  1. customMost of the solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethanol
  3. filtrationThe resulted precipitate was collected by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-42764128e5c042eab751f33af6359458
Source dataset
uspto-grants-2006_09
Patent number
US07105562B2

Reaction notes

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