benzilonium bromide

Chemical properties

Light Brown Solid

Originator

Pharm Chemical

The Uses of benzilonium bromide

An anticholinergic drug.

Manufacturing Process

A mixture containing of 23 g of 1-ethyl-3-hydroxypyrrolidine, 51.2 g of ethylbenzilate and 1.50 ml of benzene is subjected to azeotropic distillation to remove traces of water and then 250 mg of metallic sodium added to the residual solution. The mixture heated under reflux for about 8 hours while slowly drawing off the benzene-alcohol azeotrope formed. The reaction mixture is cooled, treated with 1 ml of acetic acid and washed with water. The benzene is removed by distillation and the residue distilled in vacuo to obtain the desired 1-ethyl-3-pyrrolidinyl benzilate as a viscous oil; yield 44 g, 68.1%; b.p. 164-170°C at 0.2 mm.
If desired, this same product can be prepared by adding 8 g of 1-ethyl-3- hydroxypyrrolidine in about 40 ml of dry methylene dichloride to 18.4 g of diphenylchloroacetyl chloride in about 40 ml of boiling methylene dichloride and refluxing the mixture for 1 hour. The solvent is evaporated and the residue heated on a steam bath with 200 ml of water for 5 min and then allowed to stand at room temperature for 2 days. The mixture is treated with potassium carbonate, extracted with benzene and the benzene distilled from the extract to obtain crude l-ethyl-3-pyrrolidinyl benzilate. Distillation in vacuo yields the pure l-ethyl-3-pyrrolidinyl benzilate; yield 8 g (31%); b.p. 197°C at 2 mm.
22 g of 1-ethyl-3-pyrrolidinyl benzilate prepared by either of the above methods is mixed with 32 g of ethyl bromide in 100 ml of isopropanol and refluxed for 1 hour to give 23 g of 1,1-diethyl-3-pyrrolidinium bromide benzilate, m.p.196-197°C.

brand name

Portyn (Parke-Davis).

Therapeutic Function

Anticholinergic