Patent GB913866 (http://l2.espacenet.com/dips/viewer?PN=GB913866&CY=gb&LG=en&DB=EPD)
Improvements in or relating to amino-norcamphane compounds
The invention comprises compounds (having an analeptic action) of the general formula:- wherein X represents 1 or 2, R1 is an aryl, cycloalkyl or heterocyclic radical which may be substituted by halogen or hydroxyl radicals, R2 is hydrogen or alkyl, and R3 and R1 represent hydrogen, alkyl, or cycloalkyl radicals, where these radicals can be the same or different or may be linked to form a ring, either directly or through a hetero atom, provided that (1) none of the radicals R1 to R1 contain more than 15 carbon atoms, (2) R3 and R4 do not simultaneously represent hydrogen, and (3) R3 and R4 do not simultaneously represent methyl when R1 is phenyl, R2 is hydrogen and X is 1; also their physiologically tolerable acid addition salts and quaternary ammonium compounds, together with a process for their preparation by alkylating the corresponding primary amine of general formula:- The alkylation may be performed by any known method, e.g. condensation with alkyl or aralkyl halides, reaction with formic acid and an aldehyde, reduction of an N-acyl derivative, reaction with a low alcohol in the presence of Raney nickel, or via a Schiff's base. The bases may then be converted into acid addition salts or quaternary ammonium derivatives. Belgian Specifications 557,666 and 557,667 and German Specifications 1,001,257 and 1,039,061 are referred to.
"The new compounds possess excellent compatability and show no secondary effects. Compared with the nearest similar compound described in the literature i.e. 2-phenyl-3-dimethylamino-bicyclo(2,2,1)-heptane, the compounds of this invention show a marked rise in activity eg. 2-(p-fluorophenyl)-3-dimethylamino-bicyclo(2,2,1)-heptane is twice as active as the known compound, whilst 2-phenyl-3-ethylamino-bicyclo(2,2,1)-heptane and 2-phenyl-3-diethylamino-bicyclo(2,2,1)-heptane are both three times as active."
In the patent they use reductive alkylation to obtain the N-alkylated compounds from 2-phenyl-3-amino-bicyclo(2,2,1)-heptane. The preparation of this latter compound is described in:
J Am Chem Soc 61 (1939) 521
J Am Chem Soc 73 (1951) 5068
J Org Chem 8 (1943) 373
Maybe it would get more interesting with the right substituents on the aromatic ring, say 2,5-dimethoxy-4-bromo for example.. ;)
Post 106478 (missing)
(Epikur: "US 5,284,976 Method of Producing Primary Amines in", Chemistry Discourse)