Ethylene Glycol → 1,4-Dioxa-8-azaspiro[4.5]decane-8-acetonitrile

HRID 1058612Notes

Reaction equation

HRID 1058612 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[N:10])[CH2:4][CH2:3]1.[CH2:11](O)[CH2:12][OH:13].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:11]1[CH2:12][O:13][C:2]2([CH2:7][CH2:6][N:5]([CH2:8][C:9]#[N:10])[CH2:4][CH2:3]2)[O:1]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 27609212-(4-oxopiperidin-1-yl)acetonitrile

Product 1

HCID 186688031,4-Dioxa-8-azaspiro[4.5]decane-8-acetonitrileYield 97.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 10.0 g of 4-oxo-1-piperidineacetonitrile, 22.6 g of ethylene glycol and 0.62 g of anhydrous p-toluenesulfonic acid in 100 ml of toluene was refluxed for 6 hours with Dean-stark dehydrating apparatus. After cooling, the reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was dried, and the solvent was evaporated to give a pale brown liquid. The resulting liquid was purified by alumina column chromatography using ethyl acetate—n-heptane (1:3) as an eluting solvent to give 12.8 g of a colorless liquid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe extract was dried
  4. customthe solvent was evaporated
  5. customto give a pale brown liquid
  6. customThe resulting liquid was purified by alumina column chromatography

Sources & evidence

ORD record
ord-1ae1f07031dc48a099b75ac4d4f0c37c
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

Loading…