Methyl iodide → 1,3-Diazaspiro(4.5)decane-2,4-dione, 3-methyl-

HRID 904134Notes

Reaction equation

HRID 904134 reaction equation
[NH:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[C:4](=[O:11])[NH:3][C:2]1=[O:12].[H-].[Na+].[CH3:15]I>CN(C)C=O>[CH3:15][N:3]1[C:4](=[O:11])[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[NH:1][C:2]1=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 127991,3-Diazaspiro[4.5]decane-2,4-dioneHCID 24758Sodium hydride

Product 1

HCID 128161,3-Diazaspiro(4.5)decane-2,4-dione, 3-methyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1,3-diazaspiro[4,5]decane-2,4-dione (4.0 g 0.078 mole) J. Prakt. Chem. 141 5-43 (1934) was added to a suspension of sodium hydride (1.14 g 50% oil dispersion) in dimethylformamide and heated at 50° C. for 1 hour, cooled, methyl iodide added (1.63 ml. 1.1 eq) and the mixture heated at 50° C. The dimethylformamide was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic extract was washed with water, dried (MgSO4), evaporated to dryness and the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.) to give the title compound as white prisms m.p. 214°-215° C. Yield 2.6 g=39%.

Workup

  1. temperaturecooled
  2. temperaturethe mixture heated at 50° C
  3. customThe dimethylformamide was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate and brine
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customthe crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.)

Sources & evidence

ORD record
ord-6a47b97dafb34aa7a6962a288169b00a
Source dataset
uspto-grants-1980_10
Patent number
US04230709

Reaction notes

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