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| | 2-Chloro-alpha-[2-dimethylaminoethyl]benzhydrol hydrochloride Basic information |
| | 2-Chloro-alpha-[2-dimethylaminoethyl]benzhydrol hydrochloride Chemical Properties |
| Melting point | 190-191° | | storage temp. | Hygroscopic, Refrigerator, under inert atmosphere | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | Stability: | Hygroscopic | | CAS DataBase Reference | 511-13-7(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 36/37/39-45 | | RIDADR | 3249 | | RTECS | DC7600000 | | HazardClass | 6.1(b) | | PackingGroup | III | | Toxicity | LD50 orally in rats: 350 mg/kg; s.c. in mice: 95 mg/kg (Lorenz) |
| | 2-Chloro-alpha-[2-dimethylaminoethyl]benzhydrol hydrochloride Usage And Synthesis |
| 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 |
| | 2-Chloro-alpha-[2-dimethylaminoethyl]benzhydrol hydrochloride Preparation Products And Raw materials |
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