1-ethylaminomethyl-5-methoxy-benzocyclobutene

摘要

Cpd. of formula (I):- Antitussive and analgesic, and intermediate for other pharmacologically active cpds. 3-10 mg./kg. intravenously shows a distinct antitussive effect in the cat. 0.3 mg./kg. in the pigeon shows a pronounced inhibitory effect upon expiratory activities. 0.3 mg./kg. in the rabbit displays a distinct morphine antagonistic effect. (II) was prepared by the reaction of 1-(aminomethyl)-5-methoxy-benzocyclobutene with acetic anhydride in absolute pyridine. 27 g. LiAlH4 mixed with 600 ml. THF and cooled. 69 g. (II) in 600 ml. THF was then stirred in and the mixture boiled for 10 hrs. under N2. Mixture was cooled and treated sequentially with 27 ml. water, 27 ml. 15% NaOH and 81 ml. water. After filtering through Celite the filtrate was dried and evaporated. The oily residue was treated with HCl in acetic acid to give (I) hydrochloride, mpt. 169-171 deg. after recryst from ethanol/ethyl acetate.