3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole → 5-Methoxy-3-(piperidin-4-yl)-1H-indole

HRID 1252054Notes

Reaction equation

HRID 1252054 reaction equation
C([N:4]1[CH:9]=[CH:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][CH:11]=2)[CH:6]=[CH:5]1)(=O)C.C(N1CCC(C2C3C(=CC=C(OC)C=3)NC=2)CC1)(=O)C>C(O)C.O=[Pt]=O.[OH-].[Na+]>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 149317413-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindoleHCID 201409353-(1-Acetyl-4-piperidyl)-5-methoxyindole

Product 1

HCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indoleYield 74.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole (3.0 g) was dissolved in hot ethanol (150 ml) and hydrogenation was carried out with Adams catalyst (0.25 g). The mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue containing 3-(1-acetyl-4-piperidyl)-5-methoxyindole. This residue was diluted with 2N aqueous sodium hydroxide solution (22 ml) and ethanol (30 ml) and refluxed for 18 hours. Ethanol was then distilled off and the residue was cooled. The precipitate was collected by filtration and recrystallized from a mixture of ethanol and water to give 5-methoxy-3-(4piperidyl)indole (1.92 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue
  4. temperaturerefluxed for 18 hours
  5. distillationEthanol was then distilled off
  6. temperaturethe residue was cooled
  7. filtrationThe precipitate was collected by filtration
  8. customrecrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-78cb878c446b42b484b0c8d4d514b6cc
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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