Methyl iodide → 7,9-Diethyl-3,6,7,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

HRID 840002Notes

Reaction equation

HRID 840002 reaction equation
[K].[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[NH:8][C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3].[CH3:21]I>CN(C)C=O>[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[N:8]([CH3:21])[C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5462222PotassiumHCID 203401897,9-Diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione2×

Product 1

HCID 203224527,9-Diethyl-3,6,7,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 ml of dimethylformamide were added 5.0 g of the potassium salt of 7,9-diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (Compound 1) and 11.9 g of methyl iodide; the mixture was stirred at room temperature for 16 hours. The mixture was then poured into 150 g of ice water and extracted with benzene. The benzene extract was washed with ice water and then dried over potassium carbonate. After removing the benzene, the residue was chromatographed through a column of silica gel (eluent, ethyl acetate), giving 2.7 g of Compound 2, mp 137° - 142° C.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with ice water
  4. dry with materialdried over potassium carbonate
  5. customAfter removing the benzene
  6. customthe residue was chromatographed through a column of silica gel (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-29662d607c2444028a944f0557916ce6
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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