Triethylamine → HCID 86671304, compound

HRID 2367889

Reaction equation

HRID 2367889 reaction equation
[CH3:1][N:2]([CH3:10])[N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl.[NH2:19][OH:20]>CO>[CH3:1][N:2]([CH3:10])[N:3]1[CH2:8][CH2:7][C:6](=[N:19][OH:20])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 567377821-(Dimethylamino)-4-piperidinone

Product 1

HCID 86671304HCID 86671304, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
37 °C

Procedure

19.2 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) and 30 g triethylamine are dissolved in 80 ml methanol. 18.8 g hydroxylamin hydrochloride is added in portions at ambient temperature. The internal temperature raises during the addition to 37° C. Then the mixture is heated to reflux for 3 hours, allowed to cool to room temperature, and then the solvent evaporated. The residue is partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer is dried over sodium sulfate, and the solvent evaporated. Thus, 14.5 g 1-Dimethylamino-piperidin-4-one oxime is obtained. 1H-NMR (CDCl3): 8.10 ppm (s, broad, 1H), 2.75 ppm (m, 6H), 2.40 ppm (m, 2H), 2.40 ppm (s, 6H).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool to room temperature
  4. customthe solvent evaporated
  5. customThe residue is partitioned between ethyl acetate and aqueous sodium bicarbonate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-26a3a45656db442682014dd6ec817748
Source dataset
uspto-grants-2014_04
Patent number
US08703165B2

Linked notes

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