GB1378241A - Amines and processes for their manufacture - Google Patents

Abstract

1378241 Ethanoanthracene derivatives CIBA-GEIGY AG 22 Feb 1972 [23 Feb 1971 17 Jan 1972] 8141/72 Heading C2C Novel 9-(2-A-3-R-propyl)-9,10-dihydro-9,10- ethanoanthracenes wherein R denotes a secondary or tertiary amino group and A denotes a free, etherified or acylated hydroxyl group, are prepared by a process in which a 9-X-9,10-dihydro-9,10-ethano-anthracene X is converted into a 2-A-3-R-propyl group and, if desired, free hydroxyl groups are converted into etherified or acylated hydroxyl groups, X denoting a 2,3- epoxy-propyl radical, which can be opened by an amine HR, or in which X is a radical corresponding to the 2-A-3-R-propyl group possessing at least one oxo group which can be reduced, or in which X is a radical corresponding to the 2-A-3-R-propyl group in which the nitrogen is bonded by one of its substituents to a double bond and optionally carries a positive charge or wherein one of the carbon atoms bonded to the nitrogen atom carries a hydroxy group which can be converted into a 2-A-3-R-propyl group by reduction, or in which X is a N-monosubstituted 2-A-3-amino-propyl radical which additionally carries, on the nitrogen atom, a radical Y<SP>1</SP> which can be split off by reduction, or in which X is a radical which can be converted into a 2-A-3-R-propyl group by hydrolysis. Intermediates are prepared from 9-(chlorocarbonylmethyl) - 9,10 - dihydro - 9,10 - ethano anthracene, e.g. (a) partial hydrogenation yields the acetaldehyde derivative which on reaction with trimethyloxosulphonium iodide yields the 9-(2,3-epoxypropyl) compound, (b) reduction in the presence of HCN yields the 9-(2- hydroxy-2-cyanoethyl) compound which on reduction with LiAlH 4 give the 9-(2-hydroxy-3- aminopropyl)-compound which may be converted to the following three derivatives, the 9- [(3-methyl-5-oxazolidinyl)methyl]-compound, the N-(p-toluenesulphonyl - 9 - (2 - hydroxy - 3- methylaminopropyl) compound and the 9-(2- oxo-5-oxazolidinylmethyl) compound. Pharmaceutical compositions in conventional forms for rectal, oral or parenteral administration and having anti-depressant activity comprises an above novel compound and a carrier or excipient.