1-{2-[4-(dibenzylamino)-2-methylpiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one → HCID 66774568, compound

HRID 1644512Notes

Reaction equation

HRID 1644512 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[C:22]([F:28])[CH:23]=[C:24]([F:27])[CH:25]=3)[CH:20]=[CH:19][C:18]2=[O:29])[CH:11]([CH3:30])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[C:22]([F:28])[CH:23]=[C:24]([F:27])[CH:25]=3)[CH:20]=[CH:19][C:18]2=[O:29])[CH:11]([CH3:30])[CH2:10]1

Participants

4

Reactant 1

HCID 667733571-{2-[4-(dibenzylamino)-2-methylpiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one2×

Product 1

HCID 66774568HCID 66774568, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-{2-[4-(dibenzylamino)-2-methylpiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one (Intermediate 214 358 mg, 0.71 mmol) in methanol (6 mL) was treated with palladium hydroxide on carbon (100 mg). The reaction was stirred at room temperature under hydrogen gas for 18 hours, filtered through celite, rinsed with methanol (100 mL), and concentrated under reduced pressure to afford 225 mg (96%) of a yellow oil.

Workup

  1. filtrationfiltered through celite
  2. washrinsed with methanol (100 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4971923548e7478b88a9dcb2d96cd52c
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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