Aluminium lithium hydride → HCID 21428722, compound

Participants

Reaction Steps

A solution of 8.7 g of 1-(indol-3-ylglyoxyloyl)-4-(o-tolyloxy)piperidine in 80 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 4.2 g of lithium aluminum hydride in 120 ml. of tetrahydrofuran. After addition is complete, the mixture is stirred and refluxed for 3 hours under nitrogen. The reaction mixture is then cooled and excess hydride is carefully destroyed with water. The mixture is filtered, the filter cake washed with tetrahydrofuran, and the tetrahydrofuran is removed under reduced pressure to give an oil. The oil is evacuated at about 3 mm. overnight, and then rubbed with a glass rod in the presence of hexane to give a white solid. the solid is recrystallized from a benzene and hexane mixture (charcoal treatment) to give off-white crystals. These crystals are recrystallized from an isopropanol and water mixture to give white flakes of 3-{2-[4-(o-tolyloxy)piperidyl]ethyl}indole, m.p. 88°-90° C.

Provenance & Evidence