Potassium Carbonate → 1-(2-Fluoro-4-nitrophenyl)piperidin-4-ol

HRID 2079596

Reaction equation

HRID 2079596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[OH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN(C)C=O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:22]1[CH2:23][CH2:24][CH:19]([OH:18])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 265982211-(2-Fluoro-4-nitrophenyl)piperidin-4-olYield 43%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4.77 g (30.0 mmol) of 3,4-difluoronitrobenzene in 100 mL of N,N-dimethylformamide were added 5.33 g (40.0 mmol) of potassium carbonate and 3.03 g (30.0 mmol) of 4-hydroxypiperidine and the mixture was stirred for 1 hour at 120° C. After the reaction mixture was cooled to room temperature, the reaction mixture was diluted with chloroform and insoluble substances were removed off by filtration. The filtrate was condensed and the residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1.5/1) to give 3.1 g (43%) of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customwere removed off by filtration
  3. customcondensed
  4. customthe residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1.5/1)

Sources & evidence

ORD record
ord-23b85eafb65d4593aaae4190a3d37c85
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Linked notes

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