Cis(+/-)1-{2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one → Cis(+/-)1-[2-(4-amino-3-methoxypiperidin-1-yl)ethyl]-5,7-difluoroquinolin-2(1H)-one

HRID 1644461Notes

Reaction equation

HRID 1644461 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H: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])[CH2:11][C@H:10]1[O:30][CH3:31])C1C=CC=CC=1>CO.C(#N)C.[OH-].[OH-].[Pd+2]>[NH2:8][C@H: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])[CH2:11][C@H:10]1[O:30][CH3:31]

Participants

4

Reactant 1

HCID 86642651Cis(+/-)1-{2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one2×

Product 1

HCID 69324517Cis(+/-)1-[2-(4-amino-3-methoxypiperidin-1-yl)ethyl]-5,7-difluoroquinolin-2(1H)-oneYield 90.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21959252Acetonitrile methanolSolvent

Procedure

Cis(±)1-{2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one (Intermediate 168, 240 mg, 0.46 mmol) was hydrogenated in methanol/acetonitrile (10 mL, 9:1) over palladium hydroxide on carbon (20%, 120 mg) at room temperature and normal pressure for 4 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to dryness under reduced pressure to give 140 mg (90%) of crude product. This was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0211814d3ed94207be342ef9303b0406
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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