Piperidine → (E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one

HRID 618127

Reaction equation

HRID 618127 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=O)=[CH:16]1.N1CCCCC1>C(O)C>[OH:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([C:10](=[O:12])/[CH:11]=[CH:24]/[C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:15][CH:16]=2)=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 17198Acetosyringone

Product 1

HCID 21850208(E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-oneYield 19.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4'-Hydroxy-3',5'-dimethoxyacetophenone (1.96 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 concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethyl acetate to give Compound 70 (0.62 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 32 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customThe obtained crude crystals
  6. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-74a841b976bc4f10a9a9ce9d1f52035d
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

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