Nomifensine maleate

A solution of N-(2-aminobenzyl)-1-phenyl-2-methylaminoethanol-1 was prepared by the reaction of α-bromo-acetophenone and (2nitrobenzyl)methylamine, followed by hydrogenation of the nitro group by means of nickel on diatomaceous earth at room temperature and reduction of the CO group by means of sodium borohydride. The intermediate thus produced was dissolved in 100 ml of methylene chloride and introduced dropwise into 125 ml of sulfuric acid at 10° to 15°C. After a short standing, the reaction mixture was poured onto ice and rendered alkaline by means of a sodium hydroxide solution. By extraction with ether, there was obtained 1,2,3,4-tetrahydro-2-methyl-4-phenyl-8-amino-isoquinoline. The base is reacted with maleic acid to give the maleate; melting point of the maleate 199° to 201°C (from ethanol).

A novel antidepressant distinguished from existing tricyclic and tetracyclic antidepressants by its bicyclic structure.

Molecular Weight:354.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:354.15795719
Monoisotopic Mass:354.15795719
Topological Polar Surface Area:104
Heavy Atom Count:26
Complexity:391
Undefined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes