Azepane → 1-[(6-Chloropyridin-3-YL)methyl]azepane

HRID 1392908

Reaktionsgleichung

Reaktionsgleichung von HRID 1392908
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8119AzepaneHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Produkt 1

HCID 201154641-[(6-Chloropyridin-3-YL)methyl]azepaneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chloro-5-(chloromethyl)pyridine (419 mg, 2.59 mmole) in 5 mL of dry acetonitrile is 512 mg (5.18 mmol) of azacycloheptane followed by 358 mg (2.59 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 340 mg (59% yield) of 1-(6-Chloro-pyridin-3-ylmethyl)-azepane. Diagnostic 1H NMR (400 MHz, CDCl3) 1.40–1.70 (m, 8H), 2.50–2.65 (m, 4H), 3.65 (s, 2H), 7.28 (d, 1H, J=8.3 Hz), 7.65–7.70 (m, 1H), 8.30 (d, 1H, J=2.1 Hz); MS 225.3 (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-c4ddc8b6b54743bebd1f66ff46b4ba10
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345038B2

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