Water → N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-hydroxy-2-(2,4,6-trimethyl-phenyl)-acetamide

HRID 2367891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367891
[CH3:1][N:2]([CH3:13])[N:3]1[CH2:8][CH2:7][C:6]([NH:11][OH:12])([C:9]#[N:10])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[CH2:28][C:29](Cl)=[O:30].O>O1CCCC1>[C:9]([C:6]1([N:11]([OH:12])[C:29](=[O:30])[CH2:28][C:21]2[C:20]([CH3:19])=[CH:25][C:24]([CH3:26])=[CH:23][C:22]=2[CH3:27])[CH2:7][CH2:8][N:3]([N:2]([CH3:13])[CH3:1])[CH2:4][CH2:5]1)#[N:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 866713051-Dimethylamino-4-hydroxyamino-piperidine-4-carbonitrile

Produkt 1

HCID 86671306N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-hydroxy-2-(2,4,6-trimethyl-phenyl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.31 g 1-Dimethylamino-4-hydroxyamino-piperidine-4-carbonitrile (from Step 2) is dissolved in 70 ml tetrahydrofuran. 3.34 g sodium bicarbonate is added, and the mixture cooled to 0° C. Then at 0° C., a solution of (2,4,6-trimethyl-phenyl)-acetyl chloride in 30 ml tetrahydrofuran is added slowly. The mixture is allowed to warm to room temperature and stirred for 4 hours. The water is added and three times extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over sodium sulfate, and the solvent is evaporated. The residue is purified by chromatography, with ethyl acetate/cyclohexane (2:1) as a solvent. Thus, 3.9 g N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-hydroxy-2-(2,4,6-trimethyl-phenyl)-acetamide is obtained. 1H-NMR (CDCl3): 8.18 ppm (s, broad, 1H), 6.86 ppm (s, 2H), 3.81 ppm (s, 2H), 2.97 ppm (m, 2H), 2.72 ppm (m, 2H), 2.52 ppm (m, 2H), 2.40 ppm (s, 6H), 2.25 ppm (s, 3H), 2.21 ppm (s, 6H), 2.12 ppm (m, 2H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionthree times extracted with ethyl acetate
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated
  7. customThe residue is purified by chromatography, with ethyl acetate/cyclohexane (2:1) as a solvent

Quellen und Nachweise

ORD-Eintrag
ord-cc7ceaacad0d4338bb960dc9f13ef1c6
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703165B2

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