Ethanol → 1,3-Diazaspiro(4.7)dodecane-2,4-dione

HRID 84156

Reaction equation

HRID 84156 reaction equation
[C:1]1(=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-]#N.[K+].[C:13](=[O:16])([O-])[O-].[NH4+:17].[NH4+:18].[CH2:19]([OH:21])C>O>[NH:17]1[C:1]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:19](=[O:21])[NH:18][C:13]1=[O:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 10403CyclooctanoneHCID 517111Ammonium Carbonate

Product 1

HCID 951951,3-Diazaspiro(4.7)dodecane-2,4-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of cyclooctanone (GA, 17 g, 135 mmol, Sigma-Aldrich) in ethanol (200 mL) and water (200 mL) were added KCN (17.5 g, 269 mmol, Sigma-Aldrich) followed by ammonium carbonate ([NH4]2CO3, 51.8 g, 539 mmol, Sigma-Aldrich). The resulting reaction mixture was stirred at 80° C. for 6 h. The reaction mixture was evaporated to dryness under reduced pressure to provide a white solid precipitate which was filtered, collected, and dried for 16 h to provide 15.9 g of the compound of formula GB, 1,3-diazaspiro[4.7]dodecane-2,4-dione (yield 73%).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. customto provide a white solid precipitate which
  4. filtrationwas filtered
  5. customcollected
  6. customdried for 16 h

Sources & evidence

ORD record
ord-f362c2660e9e4efb9d297bd821a73b2a
Source dataset
uspto-grants-2014_09
Patent number
US08846929B2

Linked notes

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