N-alkyl-N-(2-haloallyl) ethanolamines have been observed. Although substituted N- propargylethanolamines that contain no propargylic hydrogens undergo cyclization to 2- methylenemorpholines when treated with potassium hydroxide in boiling toluene or~ ylene,~ a similar treatment of N-(2-hydroxye thyl)-N, 4-dimethyl-4-amino-2-pentyne yields the seven-membered ring compound 4, 5, 5, 7-tetramethyl-2, 3, 4, 5-tetrahydro-
