Piperidine → Piperidine, 1-(4-nitrophenyl)-

HRID 1079392

Reaction equation

HRID 1079392 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][CH2:14][CH2:13][CH2:12]1>CN(C)C=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 81049Piperidine, 1-(4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of p-fluoronitrobenzene (31.8 ml) in dimethylformamide (200 ml) was ice-cooled and to this was added piperidine (60 ml) dropwise, followed by stirring with ice cooling for 2 hours. After the solvent was distilled off, the residual oily product was dissolved in ethyl acetate ester (200 ml), followed by washing in turn with aqueous saturated solution of sodium bicarbonate and water. Then, the solution was dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was recrystallized from n-hexane to obtain N-(4-nitrophenyl)piperidine as yellow crystals (52.8 g).

Workup

  1. temperaturecooled
  2. distillationAfter the solvent was distilled off
  3. dissolutionthe residual oily product was dissolved in ethyl acetate ester (200 ml)
  4. washby washing in turn with aqueous saturated solution of sodium bicarbonate and water
  5. dry with materialThen, the solution was dried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-2cf7a327371f4730a5c5bfa29490dc36
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Linked notes

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