Nitric Acid → 4-(4-Nitrophenyl)piperidine

HRID 2395628Notes

Reaction equation

HRID 2395628 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:13]([O-])([OH:15])=[O:14].O.[OH-].[K+]>S(=O)(=O)(O)O>[N+:13]([C:4]1[CH:5]=[CH:6][C:1]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[CH:2][CH:3]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 698734-Phenylpiperidine

Product 1

HCID 159258174-(4-Nitrophenyl)piperidineYield 40%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Phenylpiperidine (22 g, 0.14 mol) was dissolved in concentrated sulphuric acid (44 g) and concentrated nitric acid (12 ml) was then added dropwise such that the temperature did not rise above 5° C. The reaction was then warmed slowly to room temperature and stirred overnight. The reaction mixture was then poured into water and made basic with 2N aqueous potassium hydroxide. After extraction with ether (3×150 ml), the combined organic extracts were dried with sodium sulphate and evaporated in vacuo. Recrystallisation from diethyl ether afforded the desired product as yellow crystals (11.4 g, 40% yield), M.pt. 90°-92° C.

Workup

  1. customdid not rise above 5° C
  2. extractionAfter extraction with ether (3×150 ml)
  3. dry with materialthe combined organic extracts were dried with sodium sulphate
  4. customevaporated in vacuo
  5. customRecrystallisation from diethyl ether

Sources & evidence

ORD record
ord-9ceb34196ac548a8ab5ad2b6dba36f54
Source dataset
uspto-grants-1996_02
Patent number
US05489599

Reaction notes

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