Hydrochloric Acid → HCID 57795472, compound

HRID 1190066Notes

Reaction equation

HRID 1190066 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:15][CH2:14][C:9]3(OCC[O:10]3)[CH2:8][CH2:7]2)[CH2:5][N:4]([CH3:16])[C:3]1=[O:17].Cl>C1COCC1>[CH3:1][N:2]1[C:6]2([CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH2:7]2)[CH2:5][N:4]([CH3:16])[C:3]1=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57795511HCID 57795511, compound

Product 1

HCID 57795472HCID 57795472, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1,3-Dimethyl-9,12-dioxa-1,3-diaza-dispiro[4.2.4.2]tetradecan-2-one (3.16 g, 13.2 mmol) was dissolved in 66 mL of THF and a portion of 130 mL of 3N HCl aqueous solution was added. The resulting mixture was stirred at 50° C. for two days. THF was removed under vacuum then the remaining mixture was extracted with two portions of dichloromethane. The organic portions were combined, dried over anhydrous Na2SO4 and concentrated. The crude was purified by silica gel column chromatography using a gradient from 2% CH2Cl2:MeOH to 10% CH2Cl2:MeOH as eluent to afford 1,3-dimethyl-1,3-diaza-spiro[4.5]decane-2,8-dione (1.7 g, 66%).

Workup

  1. customTHF was removed under vacuum
  2. extractionthe remaining mixture was extracted with two portions of dichloromethane
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5af342be88a8454fb6994db6ac760df4
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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