10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one O-[2-(dimethylamino)ethyl]oxime monohydrochloride

Originator

Agedal,Bayer,W. Germany ,1969

Manufacturing Process

15 grams 5-keto-10,11-dihydrodibenzo-[a,d]cycloheptene dissolved in 225 ml of pyridine was mixed with 15 grams hydroxylamine hydrochloride, and the mixture was boiled under reflux for 22 hours. The bulk of the pyridine was then distilled off under reduced pressure, the residue was poured into water, and the aqueous mixture thus formed was extracted with ether.
The ether extract was washed with water, dried and heated to distill off the ether. The solid residue was recrystallized from a mixture of benzene and light petroleum (BP 40° to 60°C). 12.8 grams of the recrystallized oxime had a MP of 167° to 169°C.
A solution of 22 grams of the above described 5-oximino-10,11dihydrodibenzo-[a,d]cycloheptene in 120 ml benzene was treated with 7.8grams sodamide and the mixture was stirred and heated under reflux for 2 hours. At this stage, the 14.4 grams of hydrochloride of β-(dimethylamino) ethyl chloride was added and heating under reflux was continued for 16 hours. 50 ml water was then cautiously added to decompose unreacted sodamide and the benzene layer was separated and extracted with dilute (10%) aqueous hydrochloric acid.
The aqueous acid extracts were made alkaline with concentrated aqueous potassium hydroxide solution and then extracted with ether. The ether extracts were dried, the solvent was removed and the residual oil was distilled under reduced pressure. The product was 14.5 grams of the fraction boiling at 160° to 164°C, under a pressure of 0.05 mm of mercury.

Therapeutic Function

Psychostimulant

Safety Profile

Poison by ingestion, subcutaneous, intravenous, intramuscular, and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and HCl.