Piperidine → Z-6-chloro-3-cyclopentylmethylene-1,3-dihydro-indol-2-one

HRID 1727954Notes

Reaction equation

HRID 1727954 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH:12]1([CH:17]=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:17]/[CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 70106CyclopentanecarbaldehydeHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 68614585Z-6-chloro-3-cyclopentylmethylene-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 1a, 6-chlorooxindole (1.16 g, 6.59 mmol) was reacted with cyclopentanecarbaldehyde (0.77 g, 7.85 mmol) (Wiley) and piperidine (0.67 g, 7.85 mmol) in methanol to give a mixture of E- and Z-6-Chloro-3-cyclopentylmethylene-1,3-dihydro-indol-2-one as a brown oil (Yield 0.8 g, 49%).

Workup

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Sources & evidence

ORD record
ord-f72d12984670483e87f41499dc8e29de
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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