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

  • Barger, George, 1878-1939.
Date:
1909
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

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

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    p-M ethoxy phenylpropionamide, MeO,C0H4,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. C10H13O2N requires N = 7'8 per cent. p-M ethoxy phenylethylamine, MeO,CGH4*CH2,CH2*NH2. 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. C9H]80N,HC1 requires Cl = 18‘8 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-hydroxyphenylethylamine, melting at 169—170°, was isolated. The Wellcome Physiological Research Laboratories, Herne Hill, London, S.E. H‘ CLAY AND SONS, LTD., BREAD STREET HULL, E.C., AND BUNGAY, SUFFOLK.