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

HRID 255379Notes

Reaction equation

HRID 255379 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-726c61373adf48e79761d9b69b0f9188
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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