Synthesis of cotarnine / by Arthur H. Salway.

  • Salway, Arthur Henry.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Synthesis of cotarnine / by Arthur H. Salway. 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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    precipitate of acid amide thus formed was collected and recrystallised from alcohol, when it separated in long, colourless needles, melting at 129—130°: 0-1246 gave 0'2706 C02 and 0'0672 H20. C = 59’2; H = 60. CnHlsO,,N requires C = 59'2; H = 5’8 per cent. fi-3-M ethoxy-4: 5-methylenedioxyphenylpropionamide is readily soluble in chloroform or alcohol, but only sparingly so in ether or benzene. It may be crystallised from hot benzene, and separates from this solvent in well-formed, colourless needles. $-3-Methoxy-4 \ h-metliylenedioxyphenylethylamine (VI, p. 1209). Ninety grams of finely powdered /3-3-methoxy-4: 5-methylene- dioxyphenylpropionamide were added to 1400 c.c. of an alkaline solution of sodium hypochlorite containing 77 grams of active chlorine (compare Graebe, Ber., 1902, 35, 2753), and the mixture was shaken continuously until the amide had completely dissolved, for which about two hours were necessary. The clear solution was then heated for a short time (fifteen minutes) on the boiling-water bath, when a dark-coloured oil separated, which was extracted with ether. The ethereal solution was washed with water, and subsequently shaken with dilute hydrochloric acid until the base was completely extracted. A small portion of this acid solution, when concentrated to a small volume, yielded a crystalline hydrochloride, which was purified by recrystallisation from a mixture of absolute alcohol and ethyl acetate. It separated from this solvent in colourless needles, melting at 165°: 0-1496 gave 0'2826 C02 and 0'0850 H20. C = 51’5; H = 6'3. C10H14O3NCl requires C = 51'8] H = 60 per cent. 13-3-Methoxy-4 : 5-methylenedioxyphenylethylamine, as obtained from its hydrochloride, was a light brown oil, which did not solidify on keeping. Its benzoyl derivative crystallises from a mixture of benzene and light petroleum in shining, colourless, flat prisms, melting at 90—91°. Phenylacetyl-fi-3-methoxy-4: 5-methylenedioxyphenylethylamine (VII, p. 1209). The solution of £-3-methoxy-4: 5-methylenedioxyphenylethyl- amine hydrochloride obtained in the above reaction was directly converted into the phenylacetyl derivative by shaking with an excess of phenylacetyl chloride in the presence of alkali. After a short time the desired compound separated as a light brown solid; this was collected, and crystallised from alcohol, from which it separated in well-formed, colourless needles, melting at 103—104°;