Sodium Hydroxide → HCID 67225501, Verbindung

HRID 2367895

Reaktionsgleichung

Reaktionsgleichung von HRID 2367895
[CH3:1][N:2]([CH3:12])[N:3]1[CH2:8][CH2:7][C:6]([OH:11])([C:9]#N)[CH2:5][CH2:4]1.[OH-:13].[Na+].[C:15](=O)(O)[O-:16].[K+]>Cl.CO>[CH3:15][O:16][C:9]([C:6]1([OH:11])[CH2:7][CH2:8][N:3]([N:2]([CH3:12])[CH3:1])[CH2:4][CH2:5]1)=[O:13]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 516893Potassium BicarbonateHCID 866713081-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile

Produkt 1

HCID 67225501HCID 67225501, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel3×HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

4.2 g 1-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile is dissolved in 30 ml of a hydrochloric acid solution in methanol (10% HCl in methanol) and the reaction mixture is stirred at room temperature for 2 days. After 24 hours, the reaction vessel is saturated with hydrochloric acid gas. To bring the reaction to completion, the mixture is diluted with 100 ml methanol, saturated with hydrochloric acid gas and further stirred at room temperature overnight, then neutralized under cooling by addition of 40 ml NaOH 30% (to pH 6) and a saturated aqueous potassium bicarbonate solution (to pH 8). The solution is concentrated, the residue partitioned between ethyl acetate and water, the water layer extracted with ethyl acetate, the combined organic layer dried over sodium sulfate, and the solvent evaporated. The residue is purified by chromatography on silica gel, with ethyl acetate/methanol/triethylamine as a solvent (gradient 95/2.5/2.5 to 90/5/5). Thus, 2.27 g 1-Dimethylamino-4-hydroxy-piperidine-4-carboxylic acid methyl ester is obtained. 1H-NMR (CDCl3): 3.78 ppm (s, 3H), 2.90 ppm (s, broad, 1H), 2.82 ppm (m, 2H), 2.70 ppm (m, 2H), 2.41 ppm (s, 6H), 2.11 ppm (m, 2H), 1.69 ppm (m, 2H).

Aufarbeitung

  1. waitAfter 24 hours
  2. customthe reaction to completion
  3. stirringfurther stirred at room temperature overnight
  4. concentrationThe solution is concentrated
  5. customthe residue partitioned between ethyl acetate and water
  6. extractionthe water layer extracted with ethyl acetate
  7. dry with materialthe combined organic layer dried over sodium sulfate
  8. customthe solvent evaporated
  9. customThe residue is purified by chromatography on silica gel, with ethyl acetate/methanol/triethylamine as a solvent (gradient 95/2.5/2.5 to 90/5/5)

Quellen und Nachweise

ORD-Eintrag
ord-e40e551756bc4b35897904169c563fb1
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703165B2

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