Tetrahydrofuran → N-Methyl-p-(1-adamantyloxy)aniline

Participants

Reaction Steps

To a stirred suspension of 1.30 g. LiAlH4 in 20 ml. THF there was added 9.17 g. (0.034 mole) of N-formyl-p-(1-adamantyloxy)aniline in 200 ml. THF. Following 8 hours heating at reflux the mixture was cooled in ice and treated in turn with 1.3 ml. each of H2O and 15% NaOH and 4.9 ml. H2O. The inorganic gel was removed on a filter and the filtrate taken to dryness. The residue was recrystallized from Me2CO:SSB to give 5.96 g. (79%) of amine, N-methyl-p(1-adamantyloxy)aniline m.p. 134°-136°.

Provenance & Evidence