2-(Dimethylamino)ethanol → (6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanone

HRID 30204

Reaktionsgleichung

Reaktionsgleichung von HRID 30204
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(C)CCO.CON(C)[C:22]([CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:23]>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])[N:3]=1

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 79772-ChloropyridineHCID 23499459N-Methoxy-N,1-dimethylpiperidine-4-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 10705139(6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanoneAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

Add 2-chloropyridine (1 g, 8.8 mmole) to a mixture of n-butyl lithium (1.6 M in hexane) (22 mL, 35.2 mmole) and 2-dimethylamino-ethanol (1.56 g, 17.6 mmole) in hexane (20 mL at −78° C.) and stirred for 1 hour. Then add 1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide (3.2 g, 17.6 mmole) in hexane (5 mL) and stir the mixture for 1 hour. Quench the reaction mixture with water and extract twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, evaporate the solvent and purify the residual product by chromatography on a silica gel column to give about 1 g of the title product.

Aufarbeitung

  1. customQuench the reaction mixture with water
  2. extractionextract twice with ethyl acetate
  3. dry with materialdry the organic layer with anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify the residual product by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-8ba53a7bb5304ec9aee6b1de571bb1e3
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423050B2

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