Choline tosylate

Choline p-Toluenesulfonate Salt is a useful intermediate as well as a choline acetyltransferase (CHAT) substrate.

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.

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