Acid- 3-allyloxy-2-oxy-propyl amide

Lysergic Acid-(3 -ally loxy-2 -oxy-propyl)amide 

Endre Csanyi Katalin Pik Lajos Wolf Budapest, Hungary May 22,1975 

81 g of lysergic acid hydrazide, dissolved in 100 mL. of 0.1 N hydrochloric acid, are added to 10 mL. of a 1 N aqueous sodium nitrite solution, and thereafter 15 mL. of 1 N hydrochloric acid are added dropwise to the stirred mixture at 2° to 5° C. The mixture is stirred for an additional 15 minutes at 0° to 5° C Thereafter the mixture is neutralized with saturated sodium bicarbonate solution, and extracted in three portions with a total amount of 2L. of ether. The etheral fractions are combined, dried over anhydrous potassium carbonate, filtered, and a solution of 1.32 g. of 3-allyloxy-2-oxypropylamine in 100 mL. of isopropanol is added to the stirred filtrate. The mixture is stirred at room temperature for 4 hours, and thereafter washed with water. The aqueous phase is extracted with 2x50 mL. of chloroform. The organic solutions are combined, dried over anhydrous potassium carbonate, and evaporated to dryness. 

The dry residue is dissolved in ethanol, and converted into its maleate. Source (Karacsony 1977 1978) (approx. 70% yield). 

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