Adding a certain compound to certain chemical reactions, such as: 18513-79-6, 1,2,3,6-Tetrahydropyridine hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C5H10ClN, blongs to pyridine-derivatives compound. COA of Formula: C5H10ClN
To a slurry of 1,2,3,6-tetrahydropyridine hydrochloride (39b) (97.9 g, 818 mmol) in DCM (1.0 L) was added TEA (248 g, 2.5 mol). The mixture was cooled to 0-5 C. and then treated slowly dropwise with methane sulfonylchloride (112 g, 982 mmol), maintaining the reaction temperature<20 C. After addition the mixture was stirred a further 16 h at room temperature. The reaction was quenched by slow addition of H2O (1 L). The phases were separated. The aqueous layer was extracted with DCM (1.5 L). The combined organics were washed successively with saturated aqueous NH4Cl (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NH4Cl (500 mL), and brine (500 mL), dried over Na2SO4, filtered, and concentrated. The resultant yellow solid was triturated with DCM/petroleum ether (1:15, 500 mL). The solids were collected by filtration and dried under vacuum to provide 1-(methanesulfonyl)-1,2,3,6-tetrahydropyridine (39c) (116 g, 88% yield) as a light yellow solid, which was taken on without further purification. 1H NMR (400 MHz, CDCl3) delta 5.86 (dtd, J=1.7, 4.0, 8.1 Hz, 1H), 5.71 (dtd, J=1.2, 3.4, 8.5 Hz, 1H), 3.76 (quin, J=2.8 Hz, 2H), 3.37 (t, J=5.7 Hz, 2H), 2.81 (s, 3H), 2.26 (tt, J=2.9, 5.7 Hz, 2H)
At the same time, in my other blogs, there are other synthetic methods of this type of compound,18513-79-6, 1,2,3,6-Tetrahydropyridine hydrochloride, and friends who are interested can also refer to it.
Reference:
Patent; Pfizer Inc.; Chen, Ping; Cho-Schultz, Sujin; Deal, Judith Gail; Gallego, Gary Michael; Jalaie, Mehran; Kania, Robert Steven; Nair, Sajiv Krishnan; Ninkovic, Sacha; Orr, Suvi Tuula Marjukka; Palmer, Cynthia Louise; (169 pag.)US2019/330196; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem