Hydrochloric Acid → 4-(Piperidin-4-yl)indolin-2-one

HRID 1826711Notes

Reaction equation

HRID 1826711 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:20])[NH:15]3)=[CH:7][CH:6]=1.Cl>CO.O.C(O)(=O)C.[Pt](=O)=O>[NH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:20])[NH:15]3)[CH2:9][CH2:10]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 22135423HCID 22135423, compound

Product 1

HCID 221353964-(Piperidin-4-yl)indolin-2-oneYield 96%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-pyridin-4-yl-1,3-dihydroindol-2-one acetic acid salt (5.50 g, 20.4 mmol) in methanol (160 mL), water (70 mL) and acetic acid (30 mL) was added concentrated hydrochloric acid (2 mL) followed by platinum(IV) oxide (360 mg). The mixture was hydrogenated for three days. It was then filtered through celite, which was washed with methanol. The filtrate was evaporated and dried under high vacuum. The residue was dissolved in methanol (500 mL) and treated with a basic resin (hydroxide form) at pH=9–10. The resin was removed by filtration and washed with methanol. The filtrate was evaporated and dried under high vacuum to give 4.2 g (96%) of 4-piperidin-4-yl-1,3-dihydroindol-2-one.

Workup

  1. filtrationIt was then filtered through celite, which
  2. washwas washed with methanol
  3. customThe filtrate was evaporated
  4. customdried under high vacuum
  5. dissolutionThe residue was dissolved in methanol (500 mL)
  6. additiontreated with a basic resin (hydroxide form) at pH=9–10
  7. customThe resin was removed by filtration
  8. washwashed with methanol
  9. customThe filtrate was evaporated
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-be83986df22b4471805144d98bac5c9a
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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