GB728968A - Process for the preparation of piperazides of the lysergic acid series - Google Patents

Abstract

The invention comprises (1) a method of preparing compounds of the formula <FORM:0728968/IV (b)/1> wherein R is a lysergyl or isolysergyl residue (C15H15N2) or a dihydrolysergyl residue (C15 H17N2), and R1 and R2 are hydroxymethyl radicals or straight or branched chain alkyl radicals containing from 1 to 4 carbon atoms, which comprises conversion of peptides of lysergic, isolysergic or dihydrolysergic acid into the corresponding esters, treating these with hydrazine, converting the resulting hydrazides by treatment with sodium nitrite and a dilute acid into the corresponding azides, and condensing the latter with piperazines of the formula <FORM:0728968/IV (b)/2> (2) the following compounds-dihydrolysergyl-l-alanine-, dihydrolysergyl-d-alanine-, dihydrolysergyl - l - serene -, dihydrolysergyl - d-serine -, and dihydrolysergyl - d - valine - l : l-1 : 2 - trimethylene - 5 - isobutyl - piperazides. The examples describe the preparation of the compounds listed above by conversion of the methyl esters of dihydrolysergyl - l - alanine, - d-alanine, - l - serine, d - serine, and - d - valine respectively into the corresponding hydrazides, treating these with sodium nitrite and hydrochloric acid to form the corresponding azides and condensing the latter with 1 : 1-1 : 2-trimethylene-5-isobutyl-piperazine.