Potassium Carbonate → HCID 61151479, compound

HRID 1398087Notes

Reaction equation

HRID 1398087 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:16]1[CH2:17][CH2:18][CH:13]([OH:12])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 79341Piperidin-4-ol

Product 1

HCID 61151479HCID 61151479, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1.55 g (10 mmol) of 2-fluoro-5-nitrotoluene in 35 mL of N,N-dimethylformamide were added 1.01 g (10 mmol) of 4-hydroxypiperidine and 1.8 g (13 mmol) of potassium carbonate, and the mixture was stirred for 2 hours at 120° C. The reaction mixture was poured into ice and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline solution, and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to give 1.5 g (63%) of the title compound.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline solution
  4. dry with materialdried over with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4099089e6f0d4797a203423e4ce43df0
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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