(+)-N-(o-chlorobenzyl)-alpha-methylphenethylamine hydrochloride Chemical Properties

Melting point:

182-183° (isopropanol)

alpha 

D20 +26.3° (water)

solubility 

Methanol (Slightly), Water (Slightly, Heated)

form 

Solid

color 

White to Off-White

Safety Information

Toxicity

LD50 i.p. in mice: 103 mg/kg (Boissier et al.)

(+)-N-(o-chlorobenzyl)-alpha-methylphenethylamine hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Originator

Asenlix,Aventis

Uses

The S-enantiomer of Clobenzorex (C583000), an anorexic.

Manufacturing Process

A solution of 21.0 g (0.15 mol) of 2-chlorobenzaldehyde in 100 ml of ethanol (95%) was added to a solution of 20.5 g (0.152 mol) of D-1-phenyl-2-aminopropane in 100 ml of ethanol (95%). After standing for 15 h at room temperature, the ethanol was driven off, and the oily residue was then distilled to yield 36.2 g (94%) of D-N-(2-chlorobenzylidene)-2-amino-1- phenylpropane, boiling point 142°-146°C/0.1 mm Hg.
To the solution of 36.0 g (0.14 mol) of D-N-(2-chlorobenzylidene)-2-amino-1- phenylpropane in 200 ml of dry methanol were added, in portions, 5.3 g (0.14 mol) of sodium borohydride. The mixture was stirred for 1 h at room
temperature, and refluxed for 1 h water (100 ml) was then added and the methanol was removed in vacuo. After acidifying carefully with dilute hydrochloric acid, the solution was made alkaline by dilute sodium hydroxide, and extracted with ether. 33.0 g (90%) of D-N-(1-phenyl-2-propyl)-2-
chlorobenzylamine, boiling point 132°-134°C/0.1 mm Hg, were obtained by distillation.

Therapeutic Function

Anorexic

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