DE1493960

The invention comprises compounds of the formula (wherein the tertiary alkyl group contains 4 to 6 carbon atoms, the benzene ring being optionally additionally mono- or di-substituted by methyl or ethyl groups; R1 is hydrogen or C1-4 alkyl; and R2 is hydrogen, C1-6 alkyl, C7-12 aralkyl which may be substituted in the aromatic ring by 1 to 3 hydroxy, methoxy or ethoxy groups or by a methylenedioxy group, a C2-3 hydroxyalkyl group or a C7-11 phenoxyalkyl group) and acid-addition salts thereof; and their preparation (1) by reducing a compound of the formula wherein the phenyl group is substituted as in compounds I, X is =O or H, OH and Y is -CHR1.NHR2 or a group convertible thereto by reduction and, if desired, radicals which can be eliminated by hydrogenolysis are present instead of hydrogen atoms, provided that X and Y only simultaneously denote H, OH and -CHR1.NHR2 when there is at least one radical present which can be eliminated by hydrogenolysis; or (2) by reacting a compound of the formula (wherein the phenyl group is substituted as in compounds (I), R3 is hydroxy and R4 is chlorine or bromine or R3 and R4 together are an oxygen atom) with the appropriate amine R2NH2 or a compound capable of yielding this amine; or (c) treating a compound of formula (I) which contains one or two functionally modified hydroxyl groups and/or in which the amino group is present in a functionally modified form or which has the group instead of the group -CHOH.CHNHR2 to liberate the free hydroxyl and/or amino groups by hydrolysis, alcoholysis or aminolysis; or (d) by alkylating the corresponding primary amines (i.e. compounds (I) wherein R2 is hydrogen). Groups convertible by reduction to the group -CHR1.NHR2 are -CR1NOH or esters thereof, -CHR1.N3, -CN, -CHR1.NO2, -CHR1NHNH2 or substituted derivatives thereof, -C(R1)=N.NH2 or substituted derivatives thereof, -CONH2, -C(R1)=NR2, -CHR1.N=R1, -CHR1.NH.R1.OH and -CHR1.NH.acyl wherein R1 is alkylidene, aralkylidene, hydroxyalkylidene or phenoxyalkylidene. Radicals which can be eliminated by hydrogenolysis are N-benzal groups, O- or N-benzyl groups which may be substituted, carbobenzoxy groups, nitroso groups, amino groups, arylsulphonyl groups and halogen atoms. An extensive list of reducing agents is provided. Processes (a) and (b) may also be effected simultaneously. In process (c), functionally modified hydroxyl groups include acyloxy or other es