Triethylamine → 1-Methoxy-piperidin-4-one oxime

HRID 1473768Notes

Reaction equation

HRID 1473768 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl.[NH2:18][OH:19]>CO>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6](=[N:18][OH:19])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 199366531-Methoxypiperidin-4-one

Product 1

HCID 584280071-Methoxy-piperidin-4-one oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methoxy-piperidin-4-one [prepared according to Journal of Organic Chemistry (1961), 26, 1867-74] (258 g, 2.0 mol) and triethylamine (305.2 ml, 221.9 g, 4.4 mol) in methanol (3000 ml) was added hydroxylamine hydrochloride (277.6 g, 4.0 mol), and the reaction mixture heated at reflux for 1.5 hours. The solvent was evaporated, the residue diluted with diethyl ether and the suspension filtered. The filtrate was washed with water and brine, dried over sodium sulfate and concentrated. Yield: 286.25 g of 1-methoxy-piperidin-4-one oxime as a colorless, viscous oil. This material was used without further purification in the next step.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1.5 hours
  3. customThe solvent was evaporated
  4. additionthe residue diluted with diethyl ether
  5. filtrationthe suspension filtered
  6. washThe filtrate was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThis material was used without further purification in the next step

Sources & evidence

ORD record
ord-49e800df2f5c4389b5f62bf995896404
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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