Tetrahydrofuran → 6-methoxy-3-piperidin-4-yl-1H-quinolin-2-one

HRID 74562Notes

Reaction equation

HRID 74562 reaction equation
[H][H].C([N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[C:17]([OH:28])=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([O:26][CH3:27])=[CH:21][CH:20]=3)[CH2:12][CH2:11]1)C1C=CC=CC=1.C1COCC1>[Pd].CO>[CH3:27][O:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:28])[C:16]([CH:13]1[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]1)=[CH:25]2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 178418361HCID 178418361, compound2×HCID 178488020HCID 178488020, compound

Product 1

HCID 581811026-methoxy-3-piperidin-4-yl-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a hydrogen atmosphere 160 mg (0.46 mmol) 3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-6-methoxy-quinolin-2-ol and 20 mg palladium on charcoal (10%) in 30 mL MeOH were hydrogenated for 17.5 h at 50° C. at 50 psi. Then another 10 mL THF and catalyst were added and the mixture was hydrogenated for a further 2 h. Catalyst was added again and the mixture was hydrogenated overnight at 50° C. in a hydrogen atmosphere of 60 psi. After filtration of the reaction mixture the filter cake was washed with DMF and the filtrate was evaporated down. The residue was added to EtOAc, triturated with PE and filtered. The precipitate was washed with diisopropylether and dried.

Workup

  1. additionCatalyst was added again
  2. filtrationAfter filtration of the reaction mixture the filter cake
  3. washwas washed with DMF
  4. customthe filtrate was evaporated down
  5. additionThe residue was added to EtOAc
  6. customtriturated with PE
  7. filtrationfiltered
  8. washThe precipitate was washed with diisopropylether
  9. customdried

Sources & evidence

ORD record
ord-445d253aa6804732a0cb7cf1f49476a8
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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