반응 #6231

반응 방정식

2-aminomethylpyridine

4-(3-hydroxypropylthio)pyridine

triethylamine

methanesulfonyl chloride

→

desired compound

수율 25.4%

4-[3-(N-2-pyridylmethylamino)propylthio]pyridine

수율 25.4%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 30 minutes
3. 3
   세척The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
4. 4
   기타dried
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   온도After cooling
7. 7
   기타the mixture was purified by column chromatography (eluent: chloroform/methanol=25:1)

실험 절차

To a solution of 5.26 g (31.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.20 ml (37.3 mmol) of triethylamine in 150 ml of methylene chloride, 2.90 ml (37.3 mmol) of methanesulfonyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. To 6.33 g of the residue was added 2.64 ml (25.6 mmol) of 2-aminomethylpyridine. The resulting mixture was heated at 80° C. for 3 hours. After cooling, the mixture was purified by column chromatography (eluent: chloroform/methanol=25:1) to obtain 1.62 g of the desired compound (yield: 25.4%, yellow oil).

출처