N-Methylcyclohexylamine → (6-Chloro-pyridin-3-ylmethyl)-cyclohexyl-methyl-amine

HRID 1392913

Reaktionsgleichung

Reaktionsgleichung von HRID 1392913
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:11]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH3:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Produkt 1

HCID 20116048(6-Chloro-pyridin-3-ylmethyl)-cyclohexyl-methyl-amineAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chloro-5-(chloromethyl)pyridine (500 mg, 3.08 mmole) in 8 mL of dry acetonitrile is 384 mg (3.39 mmol) of N-methylcyclohexylamine followed by 468 mg (3.39 mmol) of potassium carbonate. The reaction is heated at 80° C. for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 700 mg (95% yield) of (6-Chloro-pyridin-3-ylmethyl)-cyclohexyl-methyl-amine. C13 NMR 26.1, 26.6, 28.9, 37.7, 54.5, 62.8, 124.1, 135.1, 139.5, 149.9; MS 239.3 (M+H).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bfdb167232b440dbae80b39d59a87147
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345038B2

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