Further syntheses of p-hydroxphenylethylamine / by George Barger and George Stanley Walpole.

  • Barger, George, 1878-1939
Date:
[1909?]
Catalogue details

Licence: Public Domain Mark

Credit: Further syntheses of p-hydroxphenylethylamine / by George Barger and George Stanley Walpole. Source: Wellcome Collection.

    5/8 (page 1724)
    p-Methoxyphenylpi'opionamide, MeO*C6H4*CH2*CH2*CO*NH2. The acid obtained above (46 grams) was heated on a water-bath with one molecular proportion of phosphorus pentachloride in chloroform solution until no more hydrogen chloride was evolved. On fractionally distilling the mixture, 30 grams of p-methoxy- phenylpropionyl chloride, boiling at 161—165°/15 mm., were collected. Gaseous ammonia was passed into the ethereal solution of the chloride, and gave a quantitative yield of the amide, which crystallised from alcohol in prisms, melting at 124°: 0T009 gave 7*2 c.c. N2 (moist) at 24° and 758 mm. N = 8'0. C10TI]3O2N requires N = 7’8 per cent. p-il/ethoxyphenylethylamine, MeO’CgH^CB^’CByNEL. The amide (27 grams) was heated with 7‘9 c.c. of bromine dissolved in 150 c.c. of water containing 36’5 grams of sodium hydroxide, the temperature not exceeding 55°. On extraction of the base with ether, drying, and fractionally distilling, 8 grams of p-methoxyphenylethylamine, boiling at 138—140°/20 mm., were obtained. The base forms a colourless liquid, very sparingly soluble in water. On passing hydrogen chloride into the ethereal solution of the base, a crystalline hydrochloride, melting at 206°, was obtained: 0-0946 gave 0-0717 AgCl. Cl = 18*8. C9H130N,HC1 requires Cl = 188 per cent. 0‘5 Gram of the above hydrochloride was heated for four hour? to 160° with 5 c.c. of hydrobromic acid (D 1*4). On cooling, a salt crystallised out, but could not be readily freed from the mother liquor; the excess of hydrobromic acid was therefore removed under diminished pressure, and the remaining solid boiled in alcoholic solution with charcoal. On adding ether to the filtrate, a salt separated which gave Millon’s reaction; after benzoylation, the dibenzoyl derivative of p-hydroxyphenylethylaminp, melting at 169—170°, was isolated. The Wellcome Physiological Research Laboratories, Herne Hill, London, S.E. ■i. CLAY AND SUNS, LTD., BREAD STREET UILL, E.C., AND BT'NfiAV, SUFFOLK.