Methanol → 9,12-Dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dione

HRID 2099686Notes

Reaction equation

HRID 2099686 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:12](=[O:15])([O-])[O-].[NH4+:16].[NH4+:17].[C-]#N.[K+].[CH3:21][OH:22]>O>[NH:16]1[C:8]2([CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[C:21](=[O:22])[NH:17][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 167864459,12-Dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 1,4-dioxa-spiro[4.5]decan-8-one (10.0 g, 64.0 mmol) in 64 mL of methanol was treated with a solution of ammonium carbonate (18.4 g, 192 mmol) in 64 mL of water. Potassium cyanide (6.14 g, 96.0 mmol) was added and the mixture was stirred at 65° C. for 18 h. It was cooled to room temperature and a precipitate was formed. The precipitate was collected by filtration to give a white solid and the filtrate was extracted with ethyl acetate. The portion of ethyl acetate was concentrated to afford also a white solid. Both solids were combined to afford 9,12-dioxa-1,3-diaza-dispiro[4.2.4.2]tetradecane-2,4-dione (9.80 g g, 68%)

Workup

  1. temperatureIt was cooled to room temperature
  2. customa precipitate was formed
  3. filtrationThe precipitate was collected by filtration
  4. customto give a white solid
  5. extractionthe filtrate was extracted with ethyl acetate
  6. concentrationThe portion of ethyl acetate was concentrated
  7. customto afford also a white solid

Sources & evidence

ORD record
ord-cf3c8b205ee04d7da14ac00faacd98cf
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

Loading…