1-(chloromethyl)-4-aza-1-azonia bicyclo[2.2.2]octane chloride

Synthesis

General procedure for the synthesis of 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride from triethylenediamine (DABCO) and dichloromethane: 1,4-diazabicyclo[2.2.2]octane (DABCO) (11.2 g, 0.1 mol) was dissolved in 30 mL of dichloromethane, and the reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, a white solid was obtained by filtration, washed with dichloromethane (2 x 20 mL) and dried under vacuum to afford 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride in 96% (18.7 g) yield. The product 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride was characterized as follows: 1H-NMR (500 MHz, D2O) δ 4.97 (s, 2H), 3.40 (t, J = 7.0 Hz, 6H), 3.10 (t, J = 7.5 Hz, 6H); 13C-NMR (125 MHz, D2O) δ 68.2, 51.1, 43.9.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6643 - 6646
[2] Journal of Organic Chemistry, 2017, vol. 82, # 22, p. 11792 - 11798
[3] Journal of Fluorine Chemistry, 1996, vol. 81, # 1, p. 43 - 50
[4] Chinese Journal of Chemistry, 2015, vol. 33, # 2, p. 220 - 224
[5] Patent: WO2014/68341, 2014, A2. Location in patent: Page/Page column 39