Benzoylcholine Iodide and Chloride

BENZOYLCHOLINE IODIDE AND CHLORIDE (Choline, chloride benzoate, and Choline, iodide benzoate) 

C6HsCOC1 + H0CH2CH2C1 - C6H5C02CH2CH2C1 + HC1 C6H5C02CH2CH2C1 + Nal - C6H5C02CH2CH2I + NaCl 

2-Iodoethyl benzoate. A mixture of 170 g. of anhydrous sodium iodide and 1.2 1. of methyl ethyl ketone (Note 2) is heated on a steam bath for 1 hour with occasional shaking in a 3-1. round-bottomed flask fitted with a water-cooled reflux condenser. 2-Chloroethyl benzoate (162 g., 0.88 mole) is added to the mixture, and heating is maintained for an additional 22-24 hours with occasional shaking. The mixture is cooled to room temperature and filtered through a 15-cm. Buchner funnel with suction. The inorganic salts on the filter are washed with 200 ml. of methyl ethyl ketone, and the filtrate is concentrated by distillation of about 1 1. of the solvent. The residue is poured into 1 1. of water contained in a separatory funnel, which is shaken, and the lower layer is withdrawn. The latter is washed successively with 200 ml. of 10% sodium bisulfite solution, 200 ml. of 5% sodium bicarbonate solution, and 100 ml. of water. It is dried with anhydrous magnesium sulfate (5-7 g.) and fractionated under reduced pressure. The yield of material boiling at 133-136°/2.5 mm., n ] 1.5820, is 190 196 g. (78-81%). 

Benzoylcholine iodide. A solution of 194 g. (0.70 mole) of 2-iodocthyl benzoate in 200 ml. of dry acetone is treated with 

270 ml. of a 19.5% solution of trimethylamine in acetone (Note 3) in a 1-1. Fyrex reagent bottle which is closed with a tightly fitting rubber stopper wired in place. The solution is allowed to stand at room temperature for 24 hours (Note 4), and at the end of this time the quaternary salt is separated by filtration with suction, washed with 200 ml. of dry acetone, and air-dried (Note 5). The weight of the quaternary iodide melting with decomposition at 247° is 200-210 g. (85-90%) (Note 6). 

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