Reaktion #11528

Reaktionsgleichung

Pentylamine

potassium carbonate

sodium iodide

2-(1-adamantyl)ethyl methanesulfonate

hydrogen chloride

→

titled compound

2-(1-Adamantyl)-N-pentylethylamine hydrochloride

Lösungsmittel

ethanol

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 17 hours
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONthe concentrate was diluted with chloroform (100 ml)
4. 4
   WaschenThis was washed with a 1 N aqueous sodium hydroxide solution (100 ml)
5. 5
   Trocknena saturated aqueous sodium chloride solution (100 ml) successively, and the organic layer was dried over magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

Pentylamine (2.69 ml, 23.2 mmol), potassium carbonate (2.14 g, 15.5 mmol) and sodium iodide (2.30 g, 15.3 mmol) were added to a solution of 2-(1-adamantyl)ethyl methanesulfonate (2.07 g, 8.01 mmol) in ethanol (45.8 ml), and the mixture was refluxed for 17 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was diluted with chloroform (100 ml). This was washed with a 1 N aqueous sodium hydroxide solution (100 ml) and a saturated aqueous sodium chloride solution (100 ml) successively, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography. A 4 N solution of hydrogen chloride in ethyl acetate (3.1 ml) was added to a solution of the resulting free form (1.52 g, 6.10 mmol) of the titled compound in ethyl acetate (0.50 ml). The precipitated solid was washed with ethyl acetate and filtered off to give 1.33 g (60%) of the titled compound.

Quelle