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

HRID 2365024Notes

Reaction equation

HRID 2365024 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)=[CH:3][CH:2]=1.Cl>CO.O.C(O)(=O)C.[Pt](=O)=O>[NH:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)[CH2:5][CH2:6]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 121115814-Pyridin-4-yl-1,3-dihydro-indol-2-one

Product 1

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

Reagents, catalysts & solvents 4

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

Procedure

A suspension of 4-pyridin-4-yl-1,3-dihydro-indol-2-one (4.28 g, 20.4 mmol, prepared according to WO2002055517) in methanol (160 ml), water (70 mL) and acetic acid (30 mL) was added 37% hydrochloric acid (2 mL) and platinum(IV)oxide (360 mg). The system was hydrogenated for three days. The reaction mixture was filtered through Celite, washed with methanol. The filtrate was evaporated and dried under reduced pressure. The residue was dissolved in methanol (500 mL) and neutralized with hydroxide from resin to pH=9-10. The resin was filtered and washed with methanol, the filtrate was evaporated and concentrated under reduced pressure to give 4-piperidin-4-yl-1,3-dihydro-indol-2-one (4.2 g, 96%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated
  4. customdried under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (500 mL)
  6. filtrationThe resin was filtered
  7. washwashed with methanol
  8. customthe filtrate was evaporated
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c5d9716804d41e9a4783bc05757e689
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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