Trifluoroacetic acid → 4-[3-(Trifluoroacetylamino)propylthio]pyridine hydrochloride

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 0.70 ml (4.96 mmol) of anhydrous trifluoroacetic acid under ice-cooling with stirring and the mixture was stirred for 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 750 mg of the desired compound (free base) (68.4%, pale yellow prisms).

1. temperaturecooling
2. stirringthe mixture was stirred for at room temperature for 30 minutes
3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. customdried
5. distillationThe solvent was distilled off
6. customThe residue was purified by column chromatography (eluent: ethyl acetate)
7. customto obtain the powder which
8. washwas washed with hexane
9. customdried

ORD record

ord-51834fb593fc4ab78a89f8f120ca7a95

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389658