Alprazolam → U 43465F

Participants

Reaction Steps

The resulting solid, dimethylmethyleneammonium chloride, was suspended in tetrahydrofuran, cooled in an ice bath, treated with 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (3.09 g., 0.01 mole; and then dropwise with acetyl chloride (0.07 ml., 0.001 mole). This mixture was kept in the ice bath for 3 hours, poured into ice cold, dilute sodium bicarbonate and extracted with methylene chloride. The extract was washed with a dilute salt solution, dried over anhydrous sodium sulfate and concentrated in vacuo. A solution of the residual oil in ethanol was treated with a solution of 1 equivalent of p-toluenesulfonic acid in ethanol and the 8-chloro-1-[2-(dimethylamino)ethyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine p-toluenesulfonate was isolated by crystallization.

Provenance & Evidence