Triethylamine → 4-(3-(N-(2-thienylmethyl)amino)propylthio]pyridine

In 200 ml of methylene chloride were dissolved 10.34 g (61.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 10.2 ml (73.3 mmol) of triethylamine, methanesulfonyl chloride [5.7 ml (73.3 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. To 8.05 g of the residue was added 3.3 ml (32.5 mmol) of 2-thiophenemethylamine. 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 2.5 g of the desired compound (yield: 29.1%, 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-80d6d35a6b1b4822a93a6f325c74f83a

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246948