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 1089205Notes

Reaction equation

HRID 1089205 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH:13]2[N:16](C)[CH:10]([CH2:11][CH2:12]2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH+]1C=CC=CC=1>O>[CH2:1]([N:8]1[C:9](=[O:18])[CH:10]2[NH:16][CH:13]([CH2:12][CH2:11]2)[C:14]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2868213-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneHCID 21584435Pyridinium hydrochloride

Product 1

HCID 148395753-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-benzyl-2,4-dioxo-8-methyl-3,8-diazabicyclo(3.2.1)octane (U.S. Pat. No. 3,328,396) (1.05 g) and pyridinium hydrochloride (5 g) was heated in an oil-bath at 220° C. for 25 minutes. After cooling, the mixture was taken up with water (30 mL) and extracted with ether. The organic layer was dried over magnesium sulfate, evaporated to give 0.45 g of crude product which was chromatographed over silica gel using dichloromethane - ethyl acetate 80:20 as eluent to give 0.3 g of crystallized titled product. MP 72° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-b8ac9197a8ba45458d7fea16f15171df
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

Loading…