Process for the production of 1-aminomethyl-6-phenyl-4h-s-triazo

Details Process for the production of 1-aminomethyl-6-phenyl-4h-s-triazo Process for the production of 1-aminomethyl-6-phenyl-4h-s-triazo

1974-06-19

1976-05-18

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602472A, 2602475EP, 2602564Q, 260268TR, 260268BC, 26029359, 26029361, 260308R, C07D20948, C07D40114, C07D40306, C07D48704

Patent

active

039577619

ABSTRACT:
A multistep process for the production of a compound of the formula V: ##SPC1##
wherein R' and R" are alkyl of 1 to 3 carbon atoms, inclusive or together ##EQU1## is pyrrolidino, piperidino, 4-methylpiperazino or morpholino; and wherein the rings A and B are unsubstituted, or substituted by one or more substituents selected from the group consisting of fluoro, chloro, bromo, nitro and trifluoromethyl, which comprises treating an equivalent of a compound of formula 1: ##SPC2##
Wherein rings A and B are defined as above, with 2 equivalents of an .alpha.-phthalimido acetyl halide in an inert organic solvent to obtain a 1,3-dioxo-2-isoindolineacetic acid, [[N-(2-benzoylphenyl)-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide II which when treated with trifluoroacetic acid gives compound III; treating compound III with a dialkylmethyleneammonium chloride in an inert organic solvent to obtain a 2-[3-(dialkylamino)methyl-5-(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benz ophenone IV and treating IV with hydrazine in an alkanol to obtain a compound V above. Also claimed are the intermediates II and IV.
The 1-aminomethyltriazolobenzodiazepine compounds (V) are used for treatment of anxieties and/or depressions in mammals and birds.

REFERENCES:
patent: 3842090 (1974-10-01), Gall et al.

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