1-Benzyl-4-(1-indolyl)-piperidine → 1-(Piperidin-4-yl)-1H-indole

HRID 2258578Notes

Reaction equation

HRID 2258578 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)(=O)C>[N:14]1([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1

Participants

4

Reactant 1

HCID 212222251-Benzyl-4-(1-indolyl)-piperidine

Product 1

HCID 140907551-(Piperidin-4-yl)-1H-indoleYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A glacial acetic acid (15 mL) solution containing Pd(OH)2 /C and 1-benzyl-4-(1-indolyl)-piperidine was placed under an H2 atmosphere. The reaction temperature was raised to 80° C. After 1 hour, the reaction was cooled to room temperature and filtered. The filtrate was made basic (pH 8-9) with saturated NaHCO3, and extracted with methylene chloride. The extract was washed with water, dried, and concentrated. This material was sufficiently pure for further reactions giving 1.09 g (80% yield) of the title compound.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationfiltered
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed40eec8de5e48e791a07db527540b24
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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