Ethanol → 7,9-Diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

HRID 840001Notes

Reaction equation

HRID 840001 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[C:7](=O)[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[C-]#N.[K+].[CH2:24]([OH:26])C>>[CH2:1]([C:3]1([CH3:14])[NH:4][C:5]([CH2:12][CH3:13])([CH3:11])[CH2:6][C:7]2([NH:20][C:24](=[O:26])[NH:19][C:15]2=[O:18])[CH:8]1[CH3:9])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-one

Product 1

HCID 203401897,9-Diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Procedure

To a solution of 115 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidone in 600 ml of 50% ethanol were added 168 g of ammonium carbonate and 57.8 g of potassium cyanide; the mixture was then heated at 60° - 70° C for 8 hours. The resulting mixture was then filtered and washed with water and cold methanol, after which the solvent was evaporated off, giving 78.0 g of Compound 1, mp 263° - 267° C (decomposition).

Workup

  1. temperaturethe mixture was then heated at 60° - 70° C for 8 hours
  2. filtrationThe resulting mixture was then filtered
  3. washwashed with water and cold methanol
  4. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-11af8e4049754a9c9d36f7fb920a2145
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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