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

HRID 469323Notes

Reaction equation

HRID 469323 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:15]([OH:26])=[N:16][C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([O:24][CH3:25])=[CH:19][CH:18]=3)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].C1COCC1>[Pd].CO>[CH3:25][O:24][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:26])[C:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[CH:23]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 23938PalladiumCatalyst3×HCID 887MethanolSolvent

Procedure

A mixture of 160 mg (0.462 mmol) 3-(1-benzyl-1.2.3.6-tetrahydro-pyridin-4-yl)-6-methoxy-quinolin-2-ol and 20 mg palladium on charcoal (Pd/C 10%) in 30 mL MeOH was first of all hydrogenated for 17.5 h at 50° C. in a hydrogen atmosphere of 50 psi. Then 10 mL THF and 20 mg palladium on charcoal (Pd/C 10%) were added and hydrogenation continued for a further 2 h under the same conditions. Another 20 mg palladium on charcoal (Pd/C 10%) were added and the mixture was hydrogenated overnight at 50° C. in a hydrogen atmosphere of 60 psi. Then the reaction mixture was filtered, 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 DIPE and dried.

Workup

  1. customhydrogenated for 17.5 h
  2. customat 50° C.
  3. filtrationThen the reaction mixture was filtered
  4. washwashed with DMF
  5. customthe filtrate was evaporated down
  6. additionThe residue was added to EtOAc
  7. customtriturated with PE
  8. filtrationfiltered
  9. washThe precipitate was washed with DIPE
  10. customdried

Sources & evidence

ORD record
ord-e5d13789f9e94fd384f4f98e8539b17d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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