3-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

HRID 1089216Notes

Reaction equation

HRID 1089216 reaction equation
Cl.N1C=CC=CC=1.[CH2:8]([N:15]1[C:21](=[O:22])[CH:20]2[N:23](C)[CH:17]([CH2:18][CH2:19]2)[C:16]1=[O:25])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([N:15]1[C:16](=[O:25])[CH:17]2[NH:23][CH:20]([CH2:19][CH2:18]2)[C:21]1=[O:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2868213-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneHCID 10176127Pyridinium chloride

Product 1

HCID 148395753-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a dry flask were mixed 15 g of dry pyridine hydrochloride and 3.15 g (130 mmol) of 3-benzyl-2,4-dioxo-8-methyl-3,8-diazabicyclo [3.2.1] octane prepared according to U.S. Pat. No 3,328,398 in June 27, 1967. The mixture was heated in an oil bath preheated at 220° C. for 20 mn, cooled in an ice-bath, dissolved in 90 ml water, extracted four times with 100 ml ethyl ether. The organic layers were collected and dried over magnesium sulfate. After removing the solvent, the residue was chromatographed over silica-gel using dichloromethane/ethylacetate (80:20) to afford 1.5 g of the title compound (50%). M.P. 72° C.

Workup

  1. customprepared
  2. temperatureThe mixture was heated in an oil bath
  3. custompreheated at 220° C. for 20 mn
  4. temperaturecooled in an ice-bath
  5. extractionextracted four times with 100 ml ethyl ether
  6. customThe organic layers were collected
  7. dry with materialdried over magnesium sulfate
  8. customAfter removing the solvent
  9. customthe residue was chromatographed over silica-gel

Sources & evidence

ORD record
ord-2f4c83de04e94a7ead1cd4505aca60ce
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

Loading…