Triethylamine → Methyl 1-(4-nitrophenyl)piperidine-4-carboxylate

HRID 2206246Notes

Reaction equation

HRID 2206246 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(#N)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 424914Methyl isonipecotate

Product 1

HCID 345002Methyl 1-(4-nitrophenyl)piperidine-4-carboxylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl piperidine-4-carboxylate (2.70 g), 1-fluoro-4-nitrobenzene (6.00 g) and triethylamine (6.80 g) in acetonitrile (60 mL) was refluxed overnight, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (3.80 g).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washthe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-1b4dd148c33443aa883800ede19644ec
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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