Réaction #6237

Équation de réaction

4-(3-aminopropyloxy)pyridine

triethylamine

pivaloyl chloride

→

desired compound

Rendement 77.3%

4-(3-pivaloylaminopropyloxy) pyridine

Rendement 77.3%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 1.5 hours
3. 3
   LavageThe reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   AutreThe residue was purified by column chromatography (eluent: ethyl acetate)

Mode opératoire

To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 0.77 ml (5.52 mmol) of triethylamine in 30 ml of methylene chloride, 0.57 ml (4.63 mmol) of pivaloyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 840 mg of the desired compound (yield: 77.3%, colorless crystals).

Source