Benzyl Chloride → 7-Benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

HRID 465002Notes

Reaction equation

HRID 465002 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:11][C:10](=[O:12])[NH:9][CH2:8]2)[C:3]1=[O:13].[H-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:9]1[C:10](=[O:12])[CH2:11][C:4]2([C:3](=[O:13])[N:2]([CH3:1])[C:6](=[O:7])[CH2:5]2)[CH2:8]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 42826302-Methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

Product 1

HCID 28689347-Benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trioneYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.82 g (10 mmol) of 2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione in 20 ml N,N-dimethylformamide was added gradually under a nitrogen atmosphere to 0.05 g (10.4 mmol) of 50% oil suspension of sodium hydride which had been previously washed twice with toluene and covered with 10 ml N,N-dimethylformamide. After stirring one hour there was added 1.40 g (11 mmol) of benzyl chloride and stirring was continued overnight at room temperature. After concentrating to a small volume in vacuo, the residue was diluted with 40 ml water and extracted twice with dichloromethane. The combined organic phase was washed with water, dried over magnesium sulfate, and evaporated to give a solid. Crystallization from toluene:hexane to afford 1.74 g of 7-benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione, mp 157°-158° C.

Workup

  1. washhad been previously washed twice with toluene
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. concentrationAfter concentrating to a small volume in vacuo
  5. additionthe residue was diluted with 40 ml water
  6. extractionextracted twice with dichloromethane
  7. washThe combined organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give a solid
  11. customCrystallization from toluene

Sources & evidence

ORD record
ord-1af3cabac341455694119044d4101ce0
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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