Potassium Carbonate → 1-(3-Methoxy-4-nitrophenyl)-3,3-dimethylpiperidin-4-one

HRID 1256013Notes

Reaction equation

HRID 1256013 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][C:14]1([CH3:21])[C:19](=[O:20])[CH2:18][CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:16]2[CH2:17][CH2:18][C:19](=[O:20])[C:14]([CH3:21])([CH3:13])[CH2:15]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 222788373,3-Dimethylpiperidin-4-one2×

Product 1

HCID 580714961-(3-Methoxy-4-nitrophenyl)-3,3-dimethylpiperidin-4-oneYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoro-2-methoxy-1-nitrobenzene (1.550 g, 9.06 mmol), 3,3-dimethylpiperidin-4-one (INTERMEDIATE 38) (2.17 g, 9.06 mmol, TFA salt), and potassium carbonate (2.504 g, 18.12 mmol) in DMF (20 ml) were heated at 70° C. overnight. The reaction mixture was concentrated in vacuo to remove the solvent. The residue was partitioned between CH2Cl2 (100 mL) and water (30 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column (50%-100% CH2Cl2/Hexane) to obtain the title product (1.100 g, 43.6%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the solvent
  3. customThe residue was partitioned between CH2Cl2 (100 mL) and water (30 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-6b7d0eb2ec8a4d82947cc074fdd0a039
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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