Ethanol → 3-[5-(3-Diethylamino-propyl)-1H-indol-2-ylmethylene]-6-phenyl-1,3-dihydro-indol-2-one

HRID 1790913Notes

Reaction equation

HRID 1790913 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[CH2:23](O)[CH3:24]>>[CH2:12]([N:13]([CH2:23][CH3:24])[CH2:14][CH2:15][CH2:7][C:1]1[CH:6]=[C:21]2[C:22](=[CH:3][CH:2]=1)[NH:17][C:19]([CH:18]=[C:11]1[C:10]3[C:14](=[CH:15][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][CH:9]=3)[NH:13][C:12]1=[O:16])=[CH:20]2)[CH3:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 105363846-Phenyl-1,3-dihydro-indol-2-one

Product 1

HCID 695874143-[5-(3-Diethylamino-propyl)-1H-indol-2-ylmethylene]-6-phenyl-1,3-dihydro-indol-2-oneYield 56%

Conditions

Temperature
95 °C

Procedure

A mixture of 6-phenyl-2-oxindole (41 mg, 0.19 mmol) 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (50 mg, 0.19 mmol) and piperidine(0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 95° C. for 20 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 49 mg (56%) of the title compound as an orange crystalline solid.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-e0c06de60a0f4dbdbbee86bcceb20414
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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