The synthesis of substances allied to epinephrine / by George Barger and H.A.D. Jowett.

  • Barger, George, 1878-1939
Date:
[1905]
Catalogue details

Licence: In copyright

Credit: The synthesis of substances allied to epinephrine / by George Barger and H.A.D. Jowett. Source: Wellcome Collection.

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    OH OH j/^OH AjOH \/ \/ CH-OH | CH-NHMe CH2-NHMe CH.-OH I. II. of which I was regarded as the more probable. These views have since been confirmed by the work of Pauly (Ber., 1904, 37, 1387), Stolz (Ber., 1904, 37, 4149), and Friedmann (Beitr. chem. Physiol. Path., 1904, 6, 92), although the first-named author prefers formula II. Although we have been unable to synthesise a substance having the constitutional formula I, we have obtained its methylene and dimethyl ethers having the formulae CH2!02!C6H3*CH(0H)*CH2-NHMe and (CH30)2!C6H3*CH(0H)-CH2*NHMe respectively. As all attempts to isolate the corresponding dihydroxy-base by the decomposition of the ethers were unsuccessful, we desire to give an account of the synthesis and the properties of the compounds prepared. The synthesis was carried out as follows : an aldehyde, either piperonal or methylvanillin, was treated with magnesium methyl iodide and thus converted into the secondary alcohol, which, by loss of water, yielded the corresponding styrene. By the addition of bromine to this substance, the dibromide was formed, which by treatment with aqueous acetone yielded the bromohydrin, this product being then condensed with methylamine and the required base thus produced. The stages in the synthesis may be represented in the case of piperonal as follows : 0“CH„ o-ch9 O-CH, Ao' ^ |/\o ' Ao' —> —> \/ - \/ \/ CHO CH-OH CH i i ch3 ch2 O“0H2 o-ch0 o-ch2 /\o /\6 ' /\o . 1 -> —II \/ \/ \/ CHBr | CH-OH | CH-OH | CH2Br CH2Br CH2-NHMe The constitution of the base produced was proved by its oxidation to piperonylic or veratric acid respectively. Although we were unable to isolate the dihydroxy-base, indications of the formation of a substance having the chemical and physiological properties of epinephrine were