Patent GB-862467-A (GB)
Title: N-substituted anilides and acid addition salts thereof
IPC: C07C233/00
Filed: 1959-03-13
Abstract: The invention comprises compounds of the formula:  <FORM:0862467/IV (b)/1> in which R represents a hydrogen or halogen atom or an alkyl, alkoxy, acyloxy or acylamino radical containing up to 6 carbon atoms or a hydroxy, amino or nitro radical, R2 represents a hydrogen or halogen atom, an alkyl, alkoxy or acyloxy radical containing up to 6 carbon atoms or a hydroxy radical, R1 and R3 represent alkyl radicals containing up to 6 carbon atoms, X represents a divalent hydrocarbon radical containing 1 to 4 carbon atoms, A and B represent hydrogen atoms or methyl or ethyl radicals where A and B together contain not more than 2 carbon atoms; and acid addition salts thereof.  Compounds of the above formula, except those where R represents an amino group, may be prepared by acylating the diamine of the formula: <FORM:0862467/IV (b)/2> where R, R1, R2, X, A and B are as defined above except that R may not represent an amino group, with an acylating agent e.g. acid chloride or anhydride, containing the group R3CO, preferably on a steam bath and optionally in the presence of an organic solvent.  The compounds, except those in which R represents an amino group may also be prepared by aralkylating an anilide of the formula: p   <FORM:0862467/IV (b)/3> where R1, R2, R3, A and B are as defined above, with an aralkylating agent which will introduce the group R.C6H4.X into the anilide, for example the anilide may be reacted with an aralkyl halide of the formula R.C6H4.X-halogen, preferably in the presence of an organic solvent and acid binding agent, or the anilide may be reductively aralkylated using an aldehyde of the formula R.C6H4.Y.CHO where Y is a divalent hydrocarbon radical of 1 to 3 carbon atoms or a direct link between the aldehyde group and the ring.  The compounds in which R represents an amino group may be prepared by acylating a diamine or aralkylating an anilide in which R represents a nitro group and subsequently reducing the nitro group to an amino group.  The acid addition salts may be prepared by reacting the free amino anilide with an acid. Examples describe the preparation of compounds in which R= H, F, C2H5, OH, C2H5COO, NH2, NO2; R2= H, C2H5, OH, R1=CH3; R3=CH3, C2H5, n and iso C3H7, C4H9; A and B= H, CH3, and C2H5 and X=CH2, CH2CH2, CH2 CH2 CH2 and CH: CH. CH2.  The b.p. and m.p. of salts of other compounds of the invention are tabulated.ALSO:Analgesic compositions comprise an excipient or diluent together with a compound of the formula <FORM:0862467/VI/1> where R represents a hydrogen or halogen atom or an alkyl, alkoxy, acyloxy or acylamino radical containing up to 6 carbon atoms or an hydroxy, amino or nitro group, R2 represents a hydrogen or halogen atom, an alkyl alkoxy, or acyloxy, radical containing up to 6 carbon atoms or a hydroxy group, R1 and R3 represent alkyl radicals containing up to 6 carbon atoms, X represents a divalent hydrocarbon radical containing 1 to 4 carbon atoms and A and B represent hydrogen atoms or methyl or ethyl radicals where A and B together contain not more than 2 carbon atoms; or acid addition salts thereof.  The active compounds may be formulated as pills, capsules, tablets or powders, when mixed with suitable excipients or diluents.