Hydrochloric Acid → 1,3-Diazaspiro[4.5]decane-2,4,8-trione

HRID 518774Notes

Reaction equation

HRID 518774 reaction equation
[NH:1]1[C:5]2([CH2:14][CH2:13][C:8]3(OCC[O:9]3)[CH2:7][CH2:6]2)[C:4](=[O:15])[NH:3][C:2]1=[O:16].Cl>CCO>[NH:1]1[C:5]2([CH2:6][CH2:7][C:8](=[O:9])[CH2:13][CH2:14]2)[C:4](=[O:15])[NH:3][C:2]1=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 167864459,12-Dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dione

Product 1

HCID 667289301,3-Diazaspiro[4.5]decane-2,4,8-trione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 9,12-dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dione (6.33 g, 28.0 mmol) in HCl (6N) (28 mL, 168 mmol) and EtOH (66.0 mL) was stirred at RT for 18 hours. The mixture was partially evaporated (about ½ volume), cooled in an ice bath and brought to a pH of approximately 10. The aqueous layer was extracted with DCM (2×200 mL), and the aqueous layer concentrated. The residue was triturated with THF (2×100 mL), and solids were removed by filtration. The filtrate was evaporated to afford the title compound as a white solid.

Workup

  1. customThe mixture was partially evaporated (about ½ volume)
  2. temperaturecooled in an ice bath
  3. extractionThe aqueous layer was extracted with DCM (2×200 mL)
  4. concentrationthe aqueous layer concentrated
  5. customThe residue was triturated with THF (2×100 mL), and solids
  6. customwere removed by filtration
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-379aeb423aa94a6ab31f930ee38dfd4f
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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