Nitric Acid → HCID 13151841, compound

HRID 1448973Notes

Reaction equation

HRID 1448973 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:18])[CH3:17])=[CH:14][C:15]=2[N+:19]([O-:21])=[O:20])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 13239566HCID 13239566, compound

Product 1

HCID 13151841HCID 13151841, compound

Procedure

3 g of N-acetyl-4-(4-acetyl-phenyl)-piperidine is added at -15°, with stirring, to 20 ml of fuming nitric acid, and the reaction mixture is subsequently stirred for 30 minutes at a temperature of between 0° and 15°. It is then poured onto 100 g of ice; the pH value is adjusted to 14 with concentrated sodium hydroxide solution, and extraction is performed three times with 50 ml of methylene chloride each time. The organic phases are combined, washed until neutral, dried over sodium sulphate and concentrated in vacuo. The residue is dissolved in ether/ethanol and treated with active charcoal. The crude oily N-acetyl-4-(2-nitro-4-acetyl-phenyl)-piperidine, obtained after filtration and concentration by evaporation, can be further reacted without additional purification.

Workup

  1. extractionthe pH value is adjusted to 14 with concentrated sodium hydroxide solution, and extraction
  2. washwashed until neutral,
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in ether/ethanol
  6. additiontreated with active charcoal

Sources & evidence

ORD record
ord-16aff973dae1403eabf3a4898d8a3d60
Source dataset
uspto-grants-1980_02
Patent number
US04188396

Reaction notes

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