5-(1-Phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-one → 5-(1-Phenylpiperidin-4-yl)indolin-2-one

HRID 588279Notes

Reaction equation

HRID 588279 reaction equation
[C:1]1([N:7]2[CH2:12][CH:11]=[C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16]4)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.CO.[Pd]>[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16]4)[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 904177265-(1-Phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-one

Product 1

HCID 904184555-(1-Phenylpiperidin-4-yl)indolin-2-oneYield 67.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-one (75.8 mg, 0.261 mmol) in THF (3 ml) and MeOH (3 ml) was added 10% Pd/C (210 mg) and stirred at room temperature under H2 (1 atom) atmosphere for 2 h. The reaction mixture was filtered through a Celite pad and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to afford 5-(1-phenylpiperidin-4-yl)indolin-2-one (51.2 mg) as mixture of triphenylphosphine oxide.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-858e91197bcc4781bf20633ece499de9
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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