Reaction #6192

Reaction equation

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

stearoyl chloride

→

desired compound

Yield 95.2%

4-[3-(stearoylamino)propylthio]pyridine

Yield 95.2%

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)
7. 7
   Otherto obtain the powder which
8. 8
   Washwas washed with hexane
9. 9
   Otherdried

Procedure

To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 1.18 ml (3.48 mmol) of stearoyl 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 the powder which was washed with hexane and dried to obtain 1.20 g of the desired compound (95.2%, colorless powder), mp: 88.0°-89.0° C.

Source