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

HRID 1727958Notes

Reaction equation

HRID 1727958 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:18]=O)[CH2:17][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:18]/[CH:12]3[CH2:17][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 16275CyclohexanecarboxaldehydeHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 57507326Z-6-chloro-3-cyclohexylmethylene-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 (2 g, 11.4 mmol) was reacted with cyclohexanecarbaldehyde (1.53 g, 13.6 mmol) (Aldrich) and piperidine (1.35 mL, 13.6 mmol) in methanol to give a mixture of E- and Z-6-chloro-3-cyclohexylmethylene-1,3-dihydro-indol-2-one as a brown solid (Yield 2.71 g, 91%).

Workup

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Sources & evidence

ORD record
ord-f19fd1be99274584a03bcd93faa8fddc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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