3-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one → 3-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-one

HRID 74499Notes

Reaction equation

HRID 74499 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[N:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[NH:16][C:15]2=[O:27])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[N:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[NH:16][C:15]2=[O:27])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 183215963-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 183215593-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 44.0 g (0.123 mol) 3-(1-benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one and 10.0 g palladium (Pd/C 10%) in 500 mL methanol was hydrogenated for 16 h at 50 C in a hydrogen atmosphere of 50 psi. After filtration of the reaction mixture the solvent was eliminated in vacuo. The product was precipitated out by the addition of isopropanol. It was filtered off and dried.

Workup

  1. filtrationAfter filtration of the reaction mixture the solvent
  2. customThe product was precipitated out by the addition of isopropanol
  3. filtrationIt was filtered off
  4. customdried

Sources & evidence

ORD record
ord-265d452518a44853bbee673867b0bb01
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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