Sodium Carbonate → HCID 18970425, compound

HRID 399195Notes

Reaction equation

HRID 399195 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)=[O:4].Cl.[NH2:15][OH:16].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([N:5]1[CH2:10][CH2:9][C:8](=[N:15][OH:16])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 16639420HCID 16639420, compound

Product 1

HCID 18970425HCID 18970425, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.0 g (16 mmol) of the N-trimethylacetyl-4-piperidone obtained according to the procedure above and 1.2 g (17 mmol) of hydroxylamine hydrochloride were placed into a 50 mL flask with 20 mL of ethanol. To the resulting mixture was added 1.9 g (18 mmol) of Na2CO3, and the resulting mixture was allowed to stir at room temperature overnight. The ethanol was removed in vacuo, and the resulting solid was triturated with ethyl acetate (2×50 mL). Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL), and dried (Na2SO4). The ethyl acetate solution was concentrated to yield 2.4 g (74%) of N-trimethylacetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.75 (dd, 4H, J=12.3, 6.2 Hz), 2.68 (dd, 2H, J=6.2, 6.2 Hz), 2.39 (dd, 2H, J=6.2, 6.1 Hz), 1.36 (s, 9H); 13C NMR (75 MHz, CDCl3) δ176.66, 156.34, 45.02, 43.51, 38.77, 31.13, 28.31, 24.93.

Workup

  1. customThe ethanol was removed in vacuo
  2. customthe resulting solid was triturated with ethyl acetate (2×50 mL)
  3. washCombined ethyl acetate washings were washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationThe ethyl acetate solution was concentrated

Sources & evidence

ORD record
ord-53d45971e27c4f4cb50983805cc016a1
Source dataset
uspto-grants-1998_10
Patent number
US05817823

Reaction notes

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