GB371490A - Manufacture of alkamines - Google Patents

Abstract

Alkamines of the formula <FORM:0371490/IV/1> wherein R represents an aromatic residue which may be substituted by hydroxyl or substituted hydroxyl, X signifies alkyl, Y stands for alkyl, alkenyl, aralkyl, aralkenyl or hydrogen, and Z represents aralkyl or aralkenyl, are prepared by (1) reducing the corresponding ketone by means of sodium and alcohol and/or aqueous ether, and if desired introducing an alkyl or alkenyl group into products containing a secondary amino group; (2) introducing an aralkyl or aralkenyl residue into such alkamines of the above structure as contain a secondary amino group substituted by alkyl, alkenyl, aralkyl or aralkenyl; (3) introducing into the corresponding alkamines containing a primary amino group one or two aralkyl or aralkenyl residues, and if desired introducing an alkyl or alkenyl residue into the products. The preparation of 1-phenyl-2-methylbenzylamino-propanol-1 by methods (1) and (2) is excluded; cf Specification 318,488, [Class 2 (iii), Dyes &c.] The products possess therapeutic properties. According to the examples, (1) 1-phenyl-2-methylaminopropanol-1 is treated with cinnamyl bromide, forming 1-phenyl-2-methyl-cinnamylaminopropanol-1, and with p-methylbenzyl bromide to give 1-phenyl-2-(p-methyl-benzyl) methylaminopropanol-1; (2) 1-phenyl-2-benzylaminopropanol - 1 is produced by interaction of 1-phenyl-2-aminopropanol-1 with benzyl bromide; replacement of the benzyl bromide with cinnamyl bromide yields 1-phenyl-2-cinnamylaminopropanol-1; (3) 1-phenyl-2-benzylallylaminopropanol - 1 results from the interaction of 1-phenyl-2-benzyl-aminopropanol-1 with allyl bromide; using benzyl chloride and cinnamyl bromide, 1-phenyl-2-dibenzylaminopropanol-1 and 1-phenyl-2-benzylcinnamylaminopropanol-1 respectively are obtained; (4) the sodium compound of p-hydroxy-1-phenyl-2-methylaminopropanol-1 is first heated with benzyl bromide and the resulting p-benzyloxy-1-phenyl-2-methylaminopropanol-1 reacted with a further quantity of benzyl bromide to form p-benzyloxy-1-phenyl-2-methylbenzylaminopropanol-1. The Specification also includes the following description of the preparation of the sample:--p-methylbenzylmethylaminopropiophenone, prepared from bromopropiophenone and p-methylbenzylmethylamine, is reduced with sodium and alcohol to form 1-phenyl-2-(p-methylbenzyl)-methylaminopropanol-1. The Specification as open to inspection under Sect. 91 (3) (a) describes also the preparation of alkamines of the foregoing structure in which, in addition, any substituent may be present in the aromatic residue R, X may represent hydrogen and Y may stand for aryl. Examples are also included of the preparation of 1-phenyl-2-benzylmethylaminopropanol-1 by reduction of a -methylbenzylaminopropiophenone using sodium and alcohol or sodium and aqueous ether, and by treatment of 1-phenyl-2-methylaminopropanol-1 with benzyl chloride. This subject-matter does not appear in the Specification as accepted.