(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-4-INDANYLAMINE

Originator

Farial,Nordmark-Werke,W. Germany,1980

The Uses of (4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-4-INDANYLAMINE

Indanazoline is a sympathomimetic imidazoline derivative. Cyclopentamine showed vasoconstrictive action after local or intravenous applications.

Definition

ChEBI: Indanazoline is a member of indanes.

Manufacturing Process

38.5 g (0.1 mol) of N-4-indanyl thiourea are dissolved in 250 cc of methanol. 42,6 g (0.3 mol) of methyl iodide are added thereto and the mixture is refluxed for 2,5 hours. The mixture thereafter is cooled and the solvent is removed in a rotation evaporator in a vacuum. Thus, 57.5 g of N-4-indanyl-S_x0002_methylisothiuronium hydroiodide (86% of theoretical) are obtained. Melting point 144°C to 146°C.
33.49 (0.1 mol) of N-4-indanyl-S-methylisothiuronium hydroiodide are mixed with 9.0 g (0.15 mol) of anhydrous ethylenediamine. The mixture is slowly heated to 80°C and heating is continued until the termination of the formation of methylmercaptan (about 4 hours). After cooling the residue is dissolved in 2N hydrochloric acid and the solution is extracted with chloroform. The extract is discarded and the aqueous phase is rendered alkaline by the addition of 10% soda lye. The resulting solution is extracted with chloroform and the extract is washed with water, dried over anhydrous sodium sulfate and the solvent is removed. An oily residue is obtained which upon standing soon crystallizes.
The product is recrystallized from petroleum ether having a boiling range of 100°C to 140°C in the presence of activated carbon. Thus, 11.1 g of 2-(4- indanylamino)-2-imidazoline (55% of theoretical) are obtained as the free base. Melting point 109°C to 113°C.

Therapeutic Function

Nasal decongestant