Potassium Carbonate → 1-(2-Tetrahydrofurylmethyl)piperid-4-one oxime

HRID 622679Notes

Reaction equation

HRID 622679 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][OH:8])[CH2:3][CH2:2]1.CS(O[CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][O:16]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[O:16]1[CH2:17][CH2:18][CH2:19][CH:15]1[CH2:14][N:1]1[CH2:6][CH2:5][C:4](=[N:7][OH:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 266119(Tetrahydrofuran-2-yl)methyl methanesulfonateHCID 12849639N-Piperidin-4-ylidenehydroxylamine

Product 1

HCID 212915121-(2-Tetrahydrofurylmethyl)piperid-4-one oximeYield 535.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of piperid-4-one oxime (46 g; 0.04 moles), 2-tetrahydrofurylmethyl methanesulphonate (79.3 g; 0.44 moles) and anhydrous potassium carbonate (56.5 g; 0.40 moles) in methyl isobutyl ketone (625 ml), was boiled under reflux with stirring for 48 hours. After cooling, the reaction mixture was washed with brine, dried (Na2SO4), and the solvent removed in vacuo. The residue was crystallised from diisopropyl ether to give 1-(2-tetrahydrofurylmethyl)-piperid-4-one oxime (42.5 g), m.p. 104°-106°.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-de99814f1c6945d2932bb6a066032068
Source dataset
uspto-grants-1988_09
Patent number
US04772618

Reaction notes

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