Piperidine → 1-(3-Nitrophenyl)piperidine

HRID 324725Notes

Reaction equation

HRID 324725 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O>[N+:8]([C:4]1[CH:3]=[C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 98231-Fluoro-3-nitrobenzene

Product 1

HCID 147652751-(3-Nitrophenyl)piperidineYield 93.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-fluoronitrobenzene (10.0 g, 70.9 mmol) and piperidine (14 ml, 141 mmol) was stirred at 110° C. for 3 days. After cooling water (200 ml) was added and the mixture was extracted with dichloromethane (3×100 ml). The combined organic extracts were washed with saturated aqueous sodium carbonate, dried over sodium sulfate and evaporated to dryness to leave 1-(3-nitrophenyl)piperidine (13.7 g, 93%) as an oil. This oil was dissolved in ethanol (150 ml) and was hydrogenated at ambient pressure using palladium on activated carbon as the catalyst to yield 2a (11.7 g, 100%) as an oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (3×100 ml)
  3. washThe combined organic extracts were washed with saturated aqueous sodium carbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-6f26eb2a89f345e5bd8cf2ab791eb0cd
Source dataset
uspto-grants-2001_04
Patent number
US06218547B1

Reaction notes

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