Triethylamine → HCID 86671304, Verbindung

HRID 2367889

Reaktionsgleichung

Reaktionsgleichung von HRID 2367889
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86671304HCID 86671304, VerbindungAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-26a3a45656db442682014dd6ec817748
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703165B2

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