Sulfuric Acid → 1-benzyl-1,4-diazepan-5-one

HRID 1437243Notes

Reaction equation

HRID 1437243 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:20]=[N+]=[N-].[Na+].[OH-].[Na+]>C(O)(=O)C>[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=[O:19])[NH:20][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 33557Sodium Azide

Product 1

HCID 2397261-benzyl-1,4-diazepan-5-oneYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

Concentrated sulfuric acid (25 mL) was added to 1-benzyl-4-piperidone (10.14 g) in acetic acid (50 mL) at room temperature, and sodium azide (3.880 g) was added thereto at 0° C. over a period of 2 hours, followed by stirring at 5° C. for 25 hours. The reaction mixture was alkalinized through addition of aqueous sodium hydroxide, followed by partitioning by use of chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and then the residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (5.081 g, 47%).

Workup

  1. customby partitioning by use of chloroform
  2. extractionThe aqueous layer was extracted with chloroform
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e3637a751cd94d9385b9a38c5eee1bf7
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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