1-(1-Benzyl-piperidin-4-yl)-1,3-dihydro-indol-2-one → 1-Piperidin-4-yl-1,3-dihydro-2H-indol-2-one

HRID 1377687Notes

Reaction equation

HRID 1377687 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)[CH2:16][C:15]2=[O:23])[CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].CO>[NH: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)[CH2:16][C:15]2=[O:23])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 36559951-(1-Benzyl-piperidin-4-yl)-1,3-dihydro-indol-2-one

Product 1

HCID 27611521-Piperidin-4-yl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 10 ml of methanol containing 296 mg of 1-(1-benzyl-4-piperidyl)indol-2-one was treated with 300 mg of palladium hydroxide catalyst. The resulting suspension was hydrogenated at atmospheric pressure for 60 minutes at 23° C. More catalyst was added (100 mg) and the hydrogenation was continued for 30 minutes more. The reaction mixture was filtered through Celite, concentrated and azeotropically dried with toluene to yield 217 mg of 1-(4-piperidyl)indol-2-one.

Workup

  1. additionMore catalyst was added (100 mg)
  2. waitthe hydrogenation was continued for 30 minutes
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationconcentrated
  5. dry with materialazeotropically dried with toluene

Sources & evidence

ORD record
ord-ee99e36bb8b24fd0801d8ba1d9469d7f
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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