반응 #11528

반응 방정식

Pentylamine

potassium carbonate

sodium iodide

2-(1-adamantyl)ethyl methanesulfonate

hydrogen chloride

→

titled compound

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

용매

ethanol

ethyl acetate

ethyl acetate

반응 조건

후처리

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

실험 절차

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.

출처