Nitric Acid → 4-(4-Nitrophenyl)piperidine

HRID 409678

Reaction equation

HRID 409678 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[C:10]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>CC(O)=O>[N+:6]([C:13]1[CH:12]=[CH:11][C:10]([CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)=[CH:15][CH:14]=1)([O-:9])=[O:7]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 698734-PhenylpiperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 159258174-(4-Nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of conc. H2SO4 (2.65 mL) in AcOH (40 mL) and a solution of conc. HNO3 (2.1 mL) in AcOH (20 mL) are added sequentially and dropwise to a solution of 4-phenylpiperidine in AcOH (40 mL), maintaining the temperature below 20° C. Then, conc. H2SO4 (40 mL) is added (no cooling applied; internal temperature reaches 60° C.). The reaction mixture is allowed to cool to RT, poured onto ice/water (100 g), neutralized by addition of solid NaHCO3 (150 g), and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by trituration in Et2O to afford the title compound as a yellow solid. ESI-MS: 207.1 [MH]+; tR=2.42 min (system 1).

Workup

  1. temperaturemaintaining the temperature below 20° C
  2. customreaches 60° C.
  3. additionpoured onto ice/water (100 g)
  4. extractionextracted with DCM
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by trituration in Et2O

Sources & evidence

ORD record
ord-5f6a682a90d44a2ab2ace0188ad48486
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Linked notes

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