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

HRID 24493Notes

Reaction equation

HRID 24493 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.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH:21]=O.N1CCCCC1>C(O)C>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH:21]=[C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[CH3:1])[NH:6][C:5]1=[O:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96389Indole-2-carboxaldehydeHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 542071973-(1H-indol-2-ylmethylene)-4-methyl-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methyl-2-oxindole (147 mg), indole-2-carbaldehyde (174 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) 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 3-(1H-indol-2-ylmethylene)-4-methyl-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-360685a896a143a09b119947e666304d
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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