Synthesis
A 500 mL reactor was charged at 25 C with 50 g (268.5 mmol) methyl tosylate and 100 mL acetone to which a solution of 25.1 g (281.6 mmol) N,N-dimethyl ethanolamine in 50.3 g acetone was added continuously at 25 C over 3 h. The dropping funnel was rinsed with additional acetone. The reaction mixture was stirred at 25 C for 20 h and the reaction progress was monitored by HPLC. When the level of methyltosylate was lower than 500 ppm the resulting suspension was cooled to 0 C over 150 min and the suspension was stirred at 0 C for 60 min. The product was collected by fdtration, washed two times with 175 mL acetone and dried under vacuum at 25 C to obtain 73.1 g (99 %) of choline tosylate as a white crystalline solid.
References
[1] Russian Chemical Bulletin, 1998, vol. 47, # 8, p. 1547 - 1549
[2] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4092 - 4095
[3] Patent: JP5751578, 2015, B2. Location in patent: Paragraph 0017
[4] European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4970 - 4977
[5] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988, vol. 37, p. 2293 - 2296
