Piperidine → 1-(2,5-Dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one

HRID 618131

Reaction equation

HRID 618131 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:13])[CH3:12].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15]1.N1CCCCC1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:13])[CH:12]=[CH:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 709912',5'-Dimethoxyacetophenone

Product 1

HCID 541569131-(2,5-Dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-oneYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2',5'-Dimethoxyacetophenone (1.80 g) and indole-3-carboxaldehyde (1.45 g) were dissolved in ethanol (20 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 72 hours. The precipitated crystals were collected by filtration, and the obtained crude crystals were recrystallized from ethanol to give Compound 89 (1.35 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 72 hours
  3. filtrationThe precipitated crystals were collected by filtration
  4. customthe obtained crude crystals
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-05fe39220067459285c6760684758e9b
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

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