Urea → 9-Benzyl-3,9-diazaspiro[5.5]undecane-2,4-dione

HRID 1664807Notes

Reaction equation

HRID 1664807 reaction equation
N[C:2]([NH2:4])=[O:3].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]([CH2:22]C(O)=O)([CH2:18][C:19](O)=[O:20])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[CH2:5]([N:12]1[CH2:13][CH2:14][C:15]2([CH2:22][C:2](=[O:3])[NH:4][C:19](=[O:20])[CH2:18]2)[CH2:16][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 1176Urea3×HCID 23021129HCID 23021129, compound

Product 1

HCID 2720119-Benzyl-3,9-diazaspiro[5.5]undecane-2,4-dioneYield 104.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

Urea (242 mg, 4.03 mmol) was added to 2,2′-(1-benzylpiperidine-4,4-diyl)diacetic acid (390 mg, 1.34 mmol). The mixture was heated to 160° C. After 3 h, additional urea (242 mg, 4.03 mmol) was added and the mixture was heated to 185° C. After 18 h, additional urea (242 mg, 4.03 mmol) was added. After 48 h, the reaction mixture was allowed to cool to ambient temperature and ethanol was added. After 1 h, the mixture was filtered and solid was washed with ethanol. Saturated aqueous sodium bicarbonate was added to the solid and the suspended solution was stirred until gas release was complete. The mixture was filtered and the solid was washed with water, and concentrated to give the title compound (380 mg). MS 273.1 (M+1).

Workup

  1. temperaturethe mixture was heated to 185° C
  2. waitAfter 18 h
  3. waitAfter 48 h
  4. temperatureto cool to ambient temperature
  5. waitAfter 1 h
  6. filtrationthe mixture was filtered
  7. washsolid was washed with ethanol
  8. additionSaturated aqueous sodium bicarbonate was added to the solid
  9. filtrationThe mixture was filtered
  10. washthe solid was washed with water
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-75bf713f7c1d44bf9e04e86b5e2ab1c9
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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