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

HRID 57572

Reaction equation

HRID 57572 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 424914Methyl isonipecotate

Product 1

HCID 345002Methyl 1-(4-nitrophenyl)piperidine-4-carboxylateYield 58.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-fluoro-4-nitrobenzene (3.5 g, 24.81 mmol), methyl piperidine-4-carboxylate (4.26 g, 29.77 mmol) and K2CO3 in 40 mL of ACN, was stirred at reflux overnight. The mixture was added to 150 mL of water, extracted with EA, dried over Na2SO4. The volatiles were removed in vacuo, and the residue was purified by chromatography with PE/EA (10:1˜2:1) to give 3.84 g of methyl 1-(4-nitrophenyl)piperidine-4-carboxylate.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with EA
  3. dry with materialdried over Na2SO4
  4. customThe volatiles were removed in vacuo
  5. customthe residue was purified by chromatography with PE/EA (10:1˜2:1)

Sources & evidence

ORD record
ord-c3d4a95262ab4a52a41411a3f3da7c02
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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