Water → 5-(Piperidin-4-yl)imidazolidine-2,4-dione

HRID 2378986Notes

Reaction equation

HRID 2378986 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)=O.[C-:16]#[N:17].[Na+].[C:19](=[O:22])([O-])[O-].[NH4+:23].[NH4+].[OH2:25]>CO>[NH:6]1[CH2:5][CH2:4][CH:3]([CH:1]2[NH:23][C:16](=[O:25])[NH:17][C:19]2=[O:22])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 552652085-(Piperidin-4-yl)imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (1.0 g, 4.7 mmol) in a mixture of water (5 mL) and methanol (10 mL) were added sodium cyanide (345 mg, 7 mmol) and ammonium carbonate (902 mg, 9.4 mmol) and heated at reflux for 6 h. The reaction mixture was cooled, removed most of the solvent. The crude product was extracted with dichloromethane, dried (Na2SO4) and removed solvent. The crude product was dissolved in dichloromethane (5 mL) and treated with trifluoroacetic acid (5 mL) for 2 h. The solvent was removed and dried. MS (ESI) 184 (M+H); Rf=1.83.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. temperatureThe reaction mixture was cooled
  4. customremoved most of the solvent
  5. extractionThe crude product was extracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. customremoved solvent
  8. dissolutionThe crude product was dissolved in dichloromethane (5 mL)
  9. additiontreated with trifluoroacetic acid (5 mL) for 2 h
  10. customThe solvent was removed
  11. customdried

Sources & evidence

ORD record
ord-1d59313633d14ef3855a59f11dfd3eb6
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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