Réaction #6241

Équation de réaction

4-(3-hydroxypropylthio)pyridine

triethylamine

dodecylamine

methanesulfonyl chloride

→

desired compound

Rendement 29.5%

4-[3-(N-dodecylamino)propylthio]pyridine

Rendement 29.5%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   LavageThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
2. 2
   Autredried
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   Températurethe mixture was heated at 80° C. for 3 hours
5. 5
   TempératureAfter cooling
6. 6
   Autrethe mixture was purified by column chromatography (eluent: chloroform/methanol=25:1)

Mode opératoire

In 120 ml of methylene chloride was dissolved 5.60 g (33.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.53 ml (39.7 mmol) of triethylamine. 3.07 ml (39.7 mmol) of methanesulfonyl chloride was added, and 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. 5.34 g (28.8 mmol) of dodecylamine was added to 7.12 g of the residue, and the 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 2.86 g of the desired compound (yield: 29.5%, yellow oil).

Source