Synthesis
Example 1: Synthesis of piperidine-1-sulfonyl chloride
A mixture of piperidine (100 g, 1.17 mol) and triethylamine (178 g, 1.76 mol) in dichloromethane (500 ml) was slowly added to a solution of sulfuryl chloride (238 g, 1.76 mol) in dichloromethane (500 ml) at 0 °C - 5 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 2 hours. After completion of the reaction, the mixture was quenched by pouring into ice water. The organic layer was separated and washed with distilled water (2 x 5 v/v). The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give an oily residue (151.3 g, 70% yield). The resulting product was characterized by nuclear magnetic resonance hydrogen spectroscopy (H NMR): H NMR (300 MHz, CDCl3) δ = 1.58-1.62 (m, 2H), 1.69-1.83 (m, 4H), 3.31-3.42 (m, 4H).
References
[1] Patent: WO2015/83066, 2015, A1. Location in patent: Page/Page column 11-12
[2] Journal of Fluorine Chemistry, 1982, vol. 20, p. 425 - 438
[3] Patent: WO2005/87721, 2005, A2. Location in patent: Page/Page column 81-82
[4] Archiv der Pharmazie (Weinheim, Germany), 1958, vol. 291, p. 7,11
[5] Bulletin de la Societe Chimique de France, 1936, vol. <5> 3, p. 2143,2146, 2149, 2150
