Reaktion #6228

Reaktionsgleichung

benzylamine

4-(3-hydroxypropylthio)pyridine

triethylamine

methanesulfonyl chloride

→

desired compound

Ausbeute 16.1%

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

Ausbeute 16.1%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   WaschenThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
3. 3
   Sonstigedried
4. 4
   workup.DISTILLATIONThen the solvent was distilled off
5. 5
   Temperaturthe mixture was heated at 80° C. for 3 hours
6. 6
   TemperaturAfter cooling
7. 7
   Sonstigethe mixture was purified by column chromatography (eluent: chloroform /methanol=25:1)

Vorschrift

In 150 ml of methylene chloride were dissolved 5.22 g (30.8 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.16 ml (37.0 mmol) of triethylamine, methanesulfonyl chloride [2.86 ml (37.0 mmol)] 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. Then the solvent was distilled off. 2.62 ml (24.0 mmol) of benzylamine was added to 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 1.0 g of the desired compound (yield: 16.1%, yellow oil).

Quelle