Benzylamine → 4-[3-(N-benzylamino)propylthio)pyridine

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).

1. additionwas added
2. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
3. customdried
4. distillationThen the solvent was distilled off
5. temperaturethe mixture was heated at 80° C. for 3 hours
6. temperatureAfter cooling
7. customthe mixture was purified by column chromatography (eluent: chloroform /methanol=25:1)

ORD record

ord-cead92d510b44868b7a17bfdcce47e62

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246948