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

HRID 2424387Notes

Reaction equation

HRID 2424387 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([O:20][CH3:21])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:21][O:20][C:13]1[CH:12]=[C:11]([N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723901PiperonylamineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 259188571-(3-Methoxy-4-nitrophenyl)piperidin-4-oneYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-piperidone hydrochloride monohydrate (10.0 g, 0.065 mol) in DMF (80 mL) are added 4-Fluoro-2-methoxy-1-nitro-benzene (10.0 g, 0.058 mol) and potassium carbonate (20.2 g), and the mixture is stirred at 70° C. for 20 h. After a filtration, the filtrate is poured into H2O (ca. 300 mL), and the resulting precipitates are collected by a filtration followed by washing with H2O for several times to give title compound (8.98 g) in 61% yield. Orange solid. 1H-NMR (400 MHz, CDCl3, δ): 2.65-2.62 (4H, m), 3.81-3.78 (4H, m), 3.98 (3H, s), 6.34 (1H, d), 6.45 (1H, dd), 8.05 (1H, d).

Workup

  1. filtrationAfter a filtration
  2. additionthe filtrate is poured into H2O (ca. 300 mL)
  3. customthe resulting precipitates
  4. filtrationare collected by a filtration
  5. washby washing with H2O for several times

Sources & evidence

ORD record
ord-f50cf3f2aa5a4c3d91c12f50c235211d
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

Loading…