7-bromo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-one → 7-Bromospiro[isoindoline-1,4'-piperidin]-3-one

HRID 390138Notes

Reaction equation

HRID 390138 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH:14]=[CH:13][NH:12][CH2:11][CH2:10]1)[NH:8][C:7]2=[O:16]>CC(O)=O.O=[Pt]=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1)[NH:8][C:7]2=[O:16]

Participants

4

Reactant 1

HCID 582957447-bromo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-one

Product 1

HCID 582957267-Bromospiro[isoindoline-1,4'-piperidin]-3-oneYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 7-bromo-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridin]-3-one (2 g, 0.0072 mol) in CH3COOH was hydrogenated in the presence of PtO2 for 1.5 h. The catalyst was removed by filtration and the filtrate was concentrated to give the crude product which was washed with saturated aq Na2CO3. The solvent was removed to give the 7-bromospiro[isoindoline-1,4′-piperidin]-3-one (2 g, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product which
  4. washwas washed with saturated aq Na2CO3
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-fa458ef465bd4795b4d1554c03548242
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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