Nitric Acid → 4-(4-Nitrophenyl)piperidine

HRID 2066708Notes

Reaction equation

HRID 2066708 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-a9d1baee254f405bad8ca5126878dec2
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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