Water → 1-[3-(Ethyloxy)-4-nitrophenyl]-4-piperidinone

HRID 419631Notes

Reaction equation

HRID 419631 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 545952291-(3-Ethoxy-4-nitrophenyl)piperidin-4-ol

Product 1

HCID 598602691-[3-(Ethyloxy)-4-nitrophenyl]-4-piperidinoneYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-[3-(ethyloxy)-4-nitrophenyl]-4-piperidinol (4.00 g, 15.0 mmol) in DCM (150 mL) was sequentially added solid NaHCO3 (6.31 g, 75.1 mmol), Dess-Martin Periodane (7.65 g, 18.0 mmol) and H2O (0.27 mL, 15.0 mmol). The reaction was then vigorously stirred at rt for 1 h. The reaction was quenched with equal volumes of saturated sodium thiosulfate (aq) and saturated NaHCO3 (aq) and allowed to stir for an additional 0.5 h. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were then dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography to afford 1-[3-(ethyloxy)-4-nitrophenyl]-4-piperidinone (2.15 g, 54%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.91 (d, J=9.3 Hz, 1H), 6.61 (dd, J=9.4, 2.6 Hz, 1H), 6.53 (d, J=2.5 Hz, 1H), 4.21 (q, J=7.0 Hz, 2H), 3.81 (t, J=6.1 Hz, 4H), 2.46-2.53 (m, 4H), 1.36 (t, J=7.0 Hz, 3H).

Workup

  1. customThe reaction was quenched with equal volumes of saturated sodium thiosulfate (aq) and saturated NaHCO3 (aq)
  2. stirringto stir for an additional 0.5 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM
  5. customThe combined organic layers were then dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fb5370546e8a48a2b4403c51d9619d95
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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