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2-CHLORO-ALPHA-[2-DIMETHYLAMINOETHYL]BENZHYDROL HYDROCHLORIDE

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2-CHLORO-ALPHA-[2-DIMETHYLAMINOETHYL]BENZHYDROL HYDROCHLORIDE Basic information

Product Name:
2-CHLORO-ALPHA-[2-DIMETHYLAMINOETHYL]BENZHYDROL HYDROCHLORIDE
Synonyms:
  • 2-Chloro-[2-(dimethylamino)ethyl]-Phenyl-benzenemethanolhydrochloride
  • 2-chloro-alpha-(2-(dimethylamino)ethyl)-alpha-phenyl-benzenemethanohydro
  • 2-chloro-alpha-(2-(dimethylamino)ethyl)-benzhydrohydrochloride
  • 2-chloro-alpha-[2-(dimethylamino)ethyl]-alpha-phenyl-benzenemethanohydro
  • detigon-bayer
  • pectolitan
  • refugal
  • sk74
CAS:
511-13-7
MF:
C17H21Cl2NO
MW:
326.26
EINECS:
208-124-9
Product Categories:
  • Amines
  • Aromatics
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
511-13-7.mol
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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)
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Safety Information

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)
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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

Raw materials

2-CHLORO-ALPHA-[2-DIMETHYLAMINOETHYL]BENZHYDROL HYDROCHLORIDESupplier

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