Sodium Carbonate → HCID 54001703, compound

HRID 1351406Notes

Reaction equation

HRID 1351406 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[NH2:2][C:1](=[N:17][OH:18])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 54001703HCID 54001703, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of tert-butyl 4-cyano-1-piperidinecarboxylate (2.69 g, 12.8 mmol), hydroxylamine hydrochloride (4.45 g, 64 mmol) and sodium carbonate (6.78 g, 64 mmol) in water (40 ml) and methanol (40 ml) was heated under reflux for 5 hours. The cooled mixture was concentrated under reduced pressure and the remaining aqueous solution extracted with ethyl acetate (3×). The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a white solid, 2.60 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. extractionthe remaining aqueous solution extracted with ethyl acetate (3×)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be3ac8f9e6a8452cb0689d4a6b75c8df
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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