Azabon

Originator

Azabon,ZYF Pharm Chemical

Uses

Stimulant (central).

Definition

ChEBI: Azabon is a member of benzenes and a sulfonamide.

Manufacturing Process

The 1,4-cyclohexane-bis(methylamine) feed line was connected to the top of the preheater in a pyrolysis tube. The pyrolysis section was heated by external electric heaters. For a typical run, the pyrolysis temperature was maintained at 385°-395°C, the feed rate was 8.4 g per minute of 1,4- cyclohexanebis(methylamine) and 1.47 g per minute of nitrogen this is a ratio of 0.885 mole of nitrogen per mole of 1,4-cyclohexanebis(methylamine) per h. The crude reaction product was collected in a chilled flask and the nitrogen and reaction gases were vented to a hood. These conditions were maintained for 15.5 h, during which time 7,849 g (55 moles) of 1,4- cyclohexanebis(methylamine) was fed to the unit. Tile total crude product obtained weighed 7,269 g. Distillation of the crude product at atmospheric pressure to a base temperature of 260°-270°C yielded 1,480 g of 3- azabicyclo[3.2.2]nonane (recrystallized from an equal weight of acetone). Gas chromatography of the filtrates of this first fraction through a 6-foot column packed with 15% Carbowax 20M on white Chromosorb indicated 1,854 g of 1,4-cyclohexanebis(metnylamine) and 721.0 g of 3-azabicyclo[3.2.2]nonane present. The remainder of the crude product was distilled at 1-5 mm to a base temperature of 200°-225°C. Thus, a total of 2,201 g (17.6 moles, 62.1% yield) of 3-azabicycla[3.2.2]nonane was produced.
To a 3 L, three-neck flask equipped with a stirrer, thremometer, and condenser was charge 30.0 g (0.24 mole) of 3-azabicyclo[3.2.2]nonane, 44.3 g (0.2 mole) of p-nitrobenzenesulfonyl chloride and 2 L of water. The pH of the reaction mixture was adjusted to 14 with a 10% solution of sodium hydroxide, the reaction mixture was then slowly heated to 75°C and heating stopped. The reaction mixture was cooled to 20°C and 44.0 g (71% of theory) of crude 3-(p-nitrobenzenesulfonyl)-3-azabicyclo[3.2.2]nonane was collected by filtration.
The crude 3-(p-nitrobenzenesulfonyl)-3-azabicyclo[3.2.2]nonane (44.0 g, 0.14 mole), 5.0 g alcohol wet Raney nickel, and 400 ml methyl alcohol were charged to an autoclave and reduced at 70°C at 1000 p.s.i. hydrogen pressure until absorption of hydrogen had stopped. The crude reduced product was filtered hot to remove the Raney nickel catalyst. The filtrate was cooled to 20°C and the solid 3-(p-ammobenzenesulfonyl)-3-azabicyclo[3.2.2]nonane was collected by filtration (38.9 g 98% theory), melting point 149°-151°C.

Therapeutic Function

Central stimulant

Raw materials

Preparation Products