Patent GB-609488-A (GB)
Title: Production of propyldiamines and acridine compounds of propyldiamines
IPC: C07D219/12
Filed: 1945-08-03
Abstract: Acridines of the general formula <FORM:0609488/IV(b)/1> , wherein R in both instances represents the same saturated non-tertiary hydrocarbon radical having from three to seven carbon atoms, are prepared by condensing in phenol 2-methoxy-6:9-dichloroacridine and a diamine of the general formula <FORM:0609488/IV(b)/2> , where R has the significance indicated above.  The bases may be converted to their salts by the addition of acids.  In examples (1) to (5), 9-[11-methyl-31-(di-n-butylamino)-propylamino]-, 9-[11-methyl-31-(di-isopropylamino)-propylamino]-, 9-[11-methyl-31-(di-isoamylamino) - propylamino]-, 9 - [11 - methyl - 31 - (di - cyclohexylamino) - propylamino]- and 9 - [11 - methyl-31-(di-isobutylamino) -propylamino]-2-methoxy-6-chloroacridines are prepared by condensing 2 - methoxy - 6 : 9 - dichloroacridine with 3 - (di - n - butylamino)-, 3 - (di - isopropylamino)-, 3 - (di - isoamylamino)-, 3 - (di - cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl-propylamines, and are converted in their corresponding dihydrochlorides; (7) the substituted acridines prepared in (1) to (5) are converted into their corresponding dihydrobromides, sulphates, nitrates, phosphates, lactates and propionates.  1 - Disubstituted - amino - 3 - butanones of the general formula <FORM:0609488/IV(b)/3> are prepared by treating the hydrochloride of an amine of the general formula <FORM:0609488/IV(b)/4> with acetone, formaldehyde and water, where R has the significance already indicated.  In examples (1) to (5), 1-di-n-butylamino-, 1-di-isopropylamino-, 1-di-isoamylamino-, 1-di-cyclohexylamino- and 1-di-isobutylamino-3-butanones are prepared.  1 - Disubstituted - amino - 3 - butanoneoximes of the general formula <FORM:0609488/IV(b)/5> , where R has the significance already indicated, are prepared by reacting 1-disubstituted-amino-3-butanones, of the general formula given above, with hydroxylamine hydrochloride.  In examples (1) to (5), 1-di-n-butylamino-, 1-di-isopropylamino-, 1 - di - isoamylamino-, 1 - di - cyclohexylamino- and 1 - di - isobutylamino - 3 - butanoneoximes are prepared.  1 - Methyl - 3 - (disubstituted amino) propylamines of the general formula <FORM:0609488/IV(b)/6> , where R has the significance already indicated, are prepared by reducing the above 1-disubstituted-amino-3-butanoneoximes, e.g. by treating an alcohol solution containing the oxime with hydrogen under pressure and heat or with metallic sodium.  In examples (1) to (5), 3-(di-n-butylamino)-, 3-(di-isopropylamino)-, 3-(di-isoamylamino)-3-(di-cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl - propylamines are obtained by reducing the corresponding oximes given above with metallic sodium in the presence of absolute alcohol.ALSO:Acridines of the general formula <FORM:0609488/IV (c)/1> wherein R in both instances represents the same saturated non-tertiary hydrocarbon radical having from three to seven carbon atoms, are prepared by condensing in phenol 2-methoxy-6 : 9-dichloroacridine and a diamine of the general formula <FORM:0609488/IV (c)/2> where R has the significance indicated above. The bases may be converted to their salts by the addition of acids. In examples (1) to (5), 9 - [11 - methyl - 31 - (di - n - butylamino) - propylamino]-, 9-[11-methyl-31-(di-isopropylamino) - propylamino]-, 9 - [11 - methyl - 31 - (di - isoamyl amino) - propylamino]-, 9 - [11 - methyl - 31 - (di - cyclohexylamino) - propylamino] - and 9 - [11 - methyl-31-(di-isobutylamino)-propylamino]-2-methoxy - 6 - chloroacridines are prepared by condensing 2 - methoxy - 6 : 9 - dichloroacridine with 3 - (di - n - butylamino)-, 3 - (di - isopropylamino)-, 3 - (di - isoamylamino)-, 3 - (di - cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl-propylamines, and converted in their corresponding dihydrochlorides; (7) the substituted acridines prepared in (1) to (5) are converted into their corresponding dihydrobromides, sulphates, nitrates, phosphates, lactates and propionates.