HEXAMETHONIUM CHLORIDE

Bistrium,Squibb,US,1951

Hexamethylene diamine (116 g), sodium carbonate (466 g), and water (800 ml) were heated to 60°C, and dimethyl sulfate (830 g) added with stirring over 1% hours keeping the temperature below 90°C. The reaction mixture was then stirred at 90°C for 2 hours, then cooled to 20°C, acetone (1,200 ml) added and the whole cooled to 0°C.
The solid formed was removed by filtration and washed with acetone (150 ml). Filtrate and washings were diluted with water to 4 liters and heated to 60°C under reflux. To this was added a solution prepared from embonic acid (388 g), sodium hydroxide (80 g) and water (5 liters), the whole refluxed for 10 minutes and thereafter allowed to cool overnight.
The resultant embonate (530 g) was filtered off, washed twice with a solution of acetone (75 ml) in water (425 ml), and dried at 100°C to give an amorphous yellow powder, MP 290°C to 291°C (with decomp.). 588 g of the embonate was dissolved in boiling water (4 liters).
Hydrobromic acid 50% w/w (325 g) diluted with water (2 liters) was added slowly at the boil and the precipitated embonic acid removed by filtering hot and washing twice with hot water (1 liter). The filtrate and washings were evaporated to dryness in a steam pan and the residue recrystallized from ethyl alcohol (1,200 ml), to yield the dibromide (320 g).

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