Sodium Carbonate → 1-(4-Amino-2-fluoro-phenyl)-piperidin-4-one

HRID 895126Notes

Reaction equation

HRID 895126 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>Cl.C(OCC)(=O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 37637811-(2-Fluoro-4-nitrophenyl)piperidin-4-one

Product 1

HCID 223856071-(4-Amino-2-fluoro-phenyl)-piperidin-4-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iron powder (16.4 g, 294 mmol) was slowly added to an ice-cold solution of 1-(2-fluoro-4-nitro-phenyl)-piperidin-4-one (7 g, 29.4 mmol), obtained in Preparation 5, in ethanolic HCl (50 ml) at 0° C. and stirred at the same temperature for 2 h. The reaction mixture was basified by the addition of sodium carbonate and pH of the solution was brought to 8. It was then diluted with ethyl acetate (100 ml) and the aqueous layer was separated. The aqueous layer was further extracted with ethyl acetate (100 ml×2). Combined organic extract was washed with water followed by brine and dried over sodium sulfate. Removal of volatiles left a pasty mass (7 g), which was used for the next step.

Workup

  1. customthe aqueous layer was separated
  2. extractionThe aqueous layer was further extracted with ethyl acetate (100 ml×2)
  3. extractionCombined organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customRemoval of volatiles
  7. waitleft a pasty mass (7 g), which

Sources & evidence

ORD record
ord-cfbf24ad9f084e0e857a029833035daf
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

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