Piperidine → 4-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 24497Notes

Reaction equation

HRID 24497 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH:22]=O.N1CCCCC1>C(O)C>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[CH:22][C:14]1[NH:15][C:16]3[C:21]([C:13]=1[CH3:12])=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5](=[O:11])[NH:6]2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2772603-Methyl-1H-indole-2-carbaldehydeHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 544808514-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-2-oxindole (147 mg), 3-methyl-indole-2-carbaldehyde (190 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (10 mg) in ethanol was held in a sealed tube at 95° C. for 4 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in a vacuum oven to give 4-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one.

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. washwashed with cold ethanol
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-bd4d01409cd2464db5c5ca42380c9ee2
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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