Piperidine → 1-(2-Methoxy-4-nitrophenyl)piperidine

HRID 1993519Notes

Reaction equation

HRID 1993519 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1012932-Bromo-5-nitroanisole

Product 1

HCID 28254311-(2-Methoxy-4-nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-5-nitroanisole (5.0 g, 21.5 mmol) and piperidine (8.5 ml) is stirred for 5 h at 105° C. under N2-atmosphere. Water (80 ml) is added and the mixture is extracted twice with CH2Cl2 (2×80 ml). The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. The crude product is dissolved in AcOEt, SiO2 is then added and the solvent evaporate off In vacuo. The resulting powder is put on top of a chromatography column (SiO2; AcOEt/hexane 9:1) and the title compound eluted with hexane/AcOEt 9:1→4:1: MS: [M+1]+=237; Rf=0.2 (AcOEt/hexane 9:1).

Workup

  1. extractionthe mixture is extracted twice with CH2Cl2 (2×80 ml)
  2. washThe organic phases are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe crude product is dissolved in AcOEt
  6. additionSiO2 is then added
  7. customthe solvent evaporate off In vacuo
  8. washthe title compound eluted with hexane/AcOEt 9:1→4:1

Sources & evidence

ORD record
ord-3dd255ab30d143e89b68187a2849a7b5
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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