Ammonia → 3-Azaspiro(5.5)undecane-2,4-dione

HRID 1761269Notes

Reaction equation

HRID 1761269 reaction equation
C(OC(=O)C)(=O)C.C([O-])(=O)C.[NH4+:12].[C:13]1([CH2:23][C:24]([OH:26])=O)([CH2:19][C:20](O)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.N>C(O)(CC)C.O>[CH2:16]1[CH2:17][CH2:18][C:13]2([CH2:23][C:24](=[O:26])[NH:12][C:20](=[O:21])[CH2:19]2)[CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 78061Cyclohexanediacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 143243-Azaspiro(5.5)undecane-2,4-dioneYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A flask is charged with 66.5 g of acetic anhydride, 66.5 g of ammonium acetate, and 100 g of 1,1-cyclohexane diacetic acid. The reaction mass is heated to 160° C.-170° C. for eight hours, eliminating by distillation the acetic acid that has formed. It is cooled to 90° C.-110° C., and 200 g of water and 100 g of secondary butyl alcohol are added. It then undergoes further cooling to room temperature, and the pH is brought to approximately 9 using 30% of aqueous ammonia. This is followed by filtration, washing the solid with water. 87.7 g of dry 3,3-pentamethylene glutarimide are obtained (yield 97%).

Workup

  1. temperatureThe reaction mass is heated to 160° C.-170° C. for eight hours
  2. distillationeliminating by distillation the acetic acid that
  3. customhas formed
  4. temperatureIt is cooled to 90° C.-110° C.
  5. filtrationThis is followed by filtration
  6. washwashing the solid with water

Sources & evidence

ORD record
ord-e54b5f9b41dd414fa68b30e63dc3ed8c
Source dataset
uspto-grants-2005_01
Patent number
US06846950B2

Reaction notes

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