909-39-7

Insidon,Geigy,W. Germany,1962

antidepressant, antipsychotic;'sigma antagonist

A solution of 5-(3-toluene-p-sulfonyloxypropyl)dibenzazepine (9.2g) and 1-(2hydroxyethyl)piperazine (8.6g) in anhydrous toluene (50 cc) is heated at boiling point under reflux for 4 hours.
After cooling, distilled water (75 cc) is added. The aqueous phase is decanted. The toluene solution is washed with distilled water (25 cc) and then extracted with N hydrohloric acid (40 cc). The hydrochloric acid solution is made alkaline to phenolphthalein with sodium hydroxide (d = 1.33).The base which separates is extracted with chloroform (50 cc). The chloroform solution is dried over anhydrous sodium sulfate and then evaporated to dryness. There are obtained 5-[3-(4-β-hydroxyethylpiperazino)propyl]dibenzazepine (7.95g), the dihydrochloride of which, crystallized from ethanol, melts at about 210°C.

Antidepressant, Antipsychotic

δ1/δ2 opioid receptor agonist; an antagonist at D25HT2 and H1 receptors; atypical antidepressantantipsychotic and anxiolytic