Some phenolic derivatives of beta-phenylethylamine / by George Barger and Arthur James Ewins.

  • Barger, George, 1878-1939
Date:
[1910?]
Catalogue details

Licence: Public Domain Mark

Credit: Some phenolic derivatives of beta-phenylethylamine / by George Barger and Arthur James Ewins. Source: Wellcome Collection.

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    0*1526 gave 0-4093 CO, and 0*0807 11,0. C = 731 • H = 59. 0*1718 ,, 14*2 c.c. N2 (moist) at 22° and 760 mm. N = 9*4. UqH9ON requires C = 73-5 ; H = 6*1 ; N = 9-5 per cent. Cli 4-1fydroxy-/3-m-tolylethylamine, 0 H< >CTI2*CH2*NH2.—0*9 Gram of p-hydroxy-m-tolylacetonitrile yielded, on reduction with 4 grams of sodium in boiling alcoholic solution, 0-62 gram of a crude hydrochloride, which was crystallised by adding ether to its concentrated solution in alcohol. From this the free base wavs obtained ; it crystallised from xylene, and, after sublimation in a vacuum, melted at 132—133°: 0-1290 gave 0-3364 CO, and 0-0910 H,0. 0 = 71-2; 11 = 7 9. C9H13ON requires C = 71*5 ; H = 8*6 per cent. The hydrochloride was also analysed : 0-1226 gave 0-0956 AgCl. Cl = 19-3. C0H13ON,HC1 requires Cl = 19*0 per cent. # The dibenzoyl derivative crystallised from dilute alcohol in long, thin needles, melting at 130—131°. The quaternary iodide, OH•CrH3Me*Clf,*ClT,*NMe3T, was obtained by boiling the base with a little methyl alcohol and a large excess of methyl iodide. It melts at 231—232°, and closely resembles borderline methiodide in solubility and other properties. 4-FIydroxy-/I-m-tolylethylamine resembles jp-hydroxy-/I-phenylethyl- amine in behaviour and derivatives. The physiological action of the former base is about one-half of the latter. Both bases give Millon’s reaction, but it is significant that, unlike ;?-hydroxy-/3-phenylethylamine, the tolyl compound does not give Morner’s reaction (green coloration after heating with sulphuric acid and formaldehyde). It would appear that substitution in the phenolic ring prevents this reaction from taking place. Preparation of 3 : 4 - Dihydroxy-/3-phenylethylamine, ho\/ch2-ch2-nh’2 • > : 4-Dimethoxy-/3-phenylethylamine was prepared from vanillin according to the method described in detail by Pictet and Finkelstein (Per., 1909, 42, 1979), and 5-2 grams of the amine boiling at 164 -1G6°/13 mm. were obtained from 20*5 grams of homoveratric acid. The amine was hydrolysed by heating with ten parts of concentrated hydrochloric acid to 170° for two hours. The hydrochloride so obtained crystallised from 90 per cent, alcohol in glistening, almost colourless