Cyclization in the Course of Clarke—Eschweiler Methylation1

AC Cope, WD Burrows

Index: Cope,A.C.; Burrows,W.D. Journal of Organic Chemistry, 1965 , vol. 30, p. 2163 - 2165

Full Text: HTML

Citation Number: 18

Abstract

1, 5-Dimethyl-4-hexenylamine (3). 4-6-Methyl-5-hepten-2-one was prepared from citral in the usual way and converted to the oxime. The oxime (64.5 g., bp 86-90'at 3 mm.) dissolved in 150 ml. of &> hydrous tetrahydrofuran (THF) was added dropwise with stirriug to a solution of 18 g. of lithium aluminum hydride in 250 ml. of THF. After 40 hr. at reflux the following were added successively with stirring: 18 ml. of water, 18 ml. of 15% sodium ...