Nitric Acid → 2-(4-Nitrobenzyl)perhydroazepine

HRID 27430Notes

Reaction equation

HRID 27430 reaction equation
[CH2:1]([CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21].[OH-].[Na+]>>[N+:20]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:3][CH:4]=1)([O-:22])=[O:21]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 33614012-Benzyl-azepane

Product 1

HCID 233428272-(4-Nitrobenzyl)perhydroazepine

Procedure

Add (drop by drop while stirring at -10° ) 10 g of 2-benzylperhydroazepine to 43 ml of concentrated sulfuric acid. Then, at the same temperature, add 33 ml of concentrated nitric acid to the thus-prepared reaction mixture and allow it to heat slowly to room temperature. Stir it for a further hour. Pour the resulting admixture into 500 g of ice, alkalize it with 6 N caustic soda solution and then extract it with diethyl ether. Dry the organic phase over sodium sulfate and distil off the solvent from the dried organic phase to obtain 12.0 g (97% of theory) of the title compound as a red oil.

Workup

  1. customto the thus-prepared reaction mixture
  2. extractionextract it with diethyl ether
  3. dry with materialDry the organic phase over sodium sulfate
  4. customdistil off the solvent from the dried organic phase

Sources & evidence

ORD record
ord-973d1d078a384e9d9293966373fef686
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Reaction notes

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