2-Chloro-alpha-[2-dimethylaminoethyl]benzhydrol hydrochloride

Originator

Abehol,Pliva

Uses

A centrally-acting cough suppressant. It has local anesthetic and antihistamine properties, and may have anticholinergic effects at high doses.

Definition

ChEBI: Chlophedianol hydrochloride is a diarylmethane.

Manufacturing Process

To a suspension of 330.0 g of sodamide (moistened with toluene) in 1500 ml of absolute ether, a solution of 1080.0 g of o-chlorobenzophenone and 350.0 g of acetonitrile in 3500 ml of absolute ether was gradually added dropwise, with stirring, such that the reaction temperature adjusted itself to 28°-30°C. The reaction mixture was stirred for 12 to 15 h at room temperature and was then added carefully to some ice water. The resulting solution was extracted 3 times with ether. The ether solution was washed with water, dried over Na2SO4, filtered, and finally concentrated. When 1 L of petroleum ether was added, 1240.0 g (96% of theoretical) of β-phenyl-β-o-chlorophenylhydroacrylonitrile (melting point 90°-92°C) precipitated.
500.0 g of the β-phenyl-β-o-chlorophenyl-hydroacrylonitrile were dissolved in 3 L of methanol and hydrogenated in the presence of 50.0 g of Raney cobalt at a temperature of 60°-70°C and a pressure of 80-85 ATM. Two moles of hydrogen were absorbed, and after separation of the methanolic solution from the catalyst, 450.0 g of 1-o-chlorophenyl-1-phenyl-3-aminopropanol-1 of melting point 117°C were obtained.
Catalytic methylation of 1-o-chlorophenyl-1-phenyl-3-aminopropanol-1 (hydrogenation in the presence of 2.2 mol of formaldehyde in aqueous methanol with Raney nickel catalyst) yielded 450.0 g of l-o-chlorophenyl-1- phenyl-3 dimethylaminopropanol-1 of melting point 120°C.
In practice it is usually used as hydrochloride.

brand name

Ulo (3M Pharmaceuticals).

Therapeutic Function

Antitussive