text: Lithium amides are usually prepared in the laboratory through the addition of a titrated solution of n-butyllithium in hexanes to a solution of the amine in ether. Dry glassware and inert atmosphere are required for these reactions. Alternatively, lithium amides may be prepared by the direct action of lithium on the corresponding amine. Typical temperatures for isomerization reactions employing lithium amides are between 0 °C and reflux (ether/hexane solvent mixtures derived from the synthesis of the lithium amide are usually used directly for isomerization reactions). An excess of the base is employed to account for impurities that consume base and reaction of the base with the ether solvent. Care should be taken when HMPA is added to lithium amide reactions, as it is a known animal carcinogen.
  Organolithium reagents may also be used; however, lower temperatures are required to avoid decomposition of the base. These reactions are most often run in hexanes.
  Aluminum amides, which are bulkier and sometimes more selective than lithium amides, are prepared from the corresponding lithium amides and diethylaluminum chloride. Reactions are usually carried out at 0 °C in an inert atmosphere, with benzene as the solvent.