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

HRID 618126Notes

Reaction equation

HRID 618126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[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>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11](=[O:13])/[CH:12]=[CH:23]/[C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:14][CH:15]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 21850309(E)-1-(3,5-Dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3',5'-Dimethoxyacetophenone (1.10 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 32 hours. The reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration, followed by recrystallization from ethanol to give Compound 69 (1.79 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 32 hours
  3. filtrationthe precipitated crystals were collected by filtration
  4. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-14f4bd9d7ada40209b16df0cc3b1eae8
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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