N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide → HCID 67233261, compound

HRID 733101Notes

Reaction equation

HRID 733101 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:29])([CH3:28])[C:20]2=[O:30])=[O:18])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>Cl.CO.[OH-].[Pd+2].[OH-]>[OH:14][C:11]1([CH2:15][NH:16][C:17]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:28])([CH3:29])[C:20]2=[O:30])=[O:18])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 67231880N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide

Product 1

HCID 67233261HCID 67233261, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of N-[(1-benzyl-4-hydroxypiperidin-4-yl)methyl]-3,3-dimethyl-2-oxoindoline-1-carboxamide (280 mg, 0.68 mmol, step 1 of Example 12) and palladium hydroxide (80 mg, 20 wt. % Pd on carbon,) in 10% HCl in methanol was stirred under H2 atmosphere for 20 h. The mixture was filtered through a pad of Celite, washed with methanol and the filtrate was concentrated to give pale yellow oil. The residue was chromatographed on silica gel column eluting with CH2Cl2/methanol/NH4OH (10:1:0.2) to give 73 mg (34%) of the title compound as clear yellow oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated
  4. customto give pale yellow oil
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with CH2Cl2/methanol/NH4OH (10:1:0.2)

Sources & evidence

ORD record
ord-8a4c0d722a1041168908d85711462e5d
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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