GB839289A - Acetylenically unsaturated ethanolamines and process for their preparation - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0839289/IV (b)/1> wherein R1, R2, R4, R5, R6 and R6 are hydrogen, alkyl, aryl, aralkyl or alkaryl, at least one of R1 and R2 being hydrogen; R3 is alkyl, hydroxyalkyl, aryl, aralkyl or alkaryl and R8 is hydrogen, alkyl, alkenyl, aryl, aralkyl, alkaryl or hydroxyalkyl; and acetyl esters thereof; specified products being the N-isobutyl-, benzyl, isopropyl- and hydroxyethyl-N-propynyl - (2) - ethanolamine and N - isopropyl - N - (4 - hydroxy - 4 - methyl - 2 - hexynyl) - ethanolamine. The compounds are prepared by reacting an oxazolidine <FORM:0839289/IV (b)/2> with an acetylene derivative R8C­CH, in a solvent, at a temperature of 0-30 DEG C., in the presence of cuprous ions and at a pressure between atmospheric and 14 inches of mercury above atmospheric. The products may subsequently be etherified or converted to esters, for example acetyl esters. Oxazolidines of the formula II used as starting materials, e.g. 3-isobutyl-, 3-t-butyl-, 2-n-butyl-3-t-butyl-, 3-t-butyl-5-phenyl-, 3-benzyl-, 2-phenyl-3-benzyl-, 2-n-propyl-3-benzyl-, 3-isopropyl-, 3-b -hydroxyethyl-, 2-phenyl-3-methyl-, 3-phenyl-, 3-t-octyl- and 2-n-propyl-3-t-octyl-, oxazolidine are made by the action of an aldehyde R1R2C:O on an ethanolamine of the formula R3NH.CR4R5.CR6R7.OH (III). Ethanolamines of the formula III are made by reacting an amine with a 1:2-epoxide or by reductive alkylation of an ethanolamine with an aldehyde or ketone and catalytic hydrogenation.