Sodium Azide → 7-(4-Chlorobenzyl)perhydroazepin-2-one

HRID 27436Notes

Reaction equation

HRID 27436 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[N-:16]=[N+]=[N-].[Na+]>>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[NH:16][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 200782Cyclohexanone, 2-p-chlorobenzyl-

Product 1

HCID 233428517-(4-Chlorobenzyl)perhydroazepin-2-oneYield 59.7%

Procedure

To an ice-cold solution of 4.47 g of 2-(4-chlorobenzyl)cyclohexanone in 100g of polyphosphoric acid add 2.6 g of sodium azide while stirring. Stir the mixture for another 1.5 hours at 0° and for a further 8 hours at room temperature, pour it into ice water and then extract it with methylene chloride. After drying the organic phase over sodium sulfate distill off the solvent to obtain 2.85 g of the title compound as a light brown oil.

Workup

  1. stirringStir the mixture for another 1.5 hours at 0°
  2. extractionextract it with methylene chloride
  3. dry with materialAfter drying the organic phase over sodium sulfate
  4. distillationdistill off the solvent

Sources & evidence

ORD record
ord-d421c50ad14346048a9c41cfa6b17e08
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Reaction notes

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