5,7-dichloro-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-one → 5,7-Dichlorospiro[isoindoline-1,4'-piperidin]-3-one

HRID 390143Notes

Reaction equation

HRID 390143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[C:7]1([CH:12]=[CH:11][NH:10][CH2:9][CH2:8]1)[NH:6][C:5]2=[O:17]>C(O)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[C:7]1([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[NH:6][C:5]2=[O:17]

Participants

4

Reactant 1

HCID 582957155,7-dichloro-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-one

Product 1

HCID 582957645,7-Dichlorospiro[isoindoline-1,4'-piperidin]-3-oneYield 73.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

H2 was sent to the solution of 5,7-dichloro-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridin]-3-one (400 mg, 1.5 mmol), PtO2 (40 mg) in acetic acid (10 mL). The mixture was stirred at rt for 2 h. The mixture was filtered, the filtrate was neutralized with satd aq NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried and concentrated to give 5,7-dichlorospiro[isoindoline-1,4′-piperidin]-3-one (300 mg, 73%). 1H NMR (CD3OD): 1.36 (m, 2H), 2.76 (m, 2H), 2.94 (m, 2H), 3.12 (m, 2H), 7.67 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7407088c91c4a509eae5fecb2e31cd5
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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