Reaction #6196

Reaction equation

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

pivaloyl chloride

→

desired compound

Yield 96.4%

4-[3-(pivaloylamino)propylthio]pyridine hydrochloride

Yield 96.4%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   WashThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Otherdried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   OtherThe residue was purified by column chromatography (eluent: ethyl acetate)

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.61 ml (4.96 mmol) of pivaloyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.01 g of the desired compound (free base) (96.4%, yellow oil).

Source