Aluminum(III) Chloride → HCID 13986144, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 113 g of the compound of Step C in 1,130 ml of dioxane was added slowly with stirring under an inert atmosphere to a suspension of 110 g of aluminium-lithium hydride and 55 g of aluminium chloride in 1,700 ml of dioxane. After 1 hour of stirring between 80° C. and 50° C. and cooling to 10° C., the excess hydride was destroyed with an ammonium chloride-dioxane-water mixture. The resulting mixture was diluted with water, filtered, and the filtrate was concentrated by eliminating about 1,000 ml of solvent. After adding water and extracting with methylene chloride, the extracts were washed with water saturated with sodium chloride, dried and evaporated to dryness to obtain 95 g of crude product. The crude product was refluxed with stirring in 1 liter of ethyl acetate and 8.5 g of insoluble matter corresponding to the hydrochloride of the expected product were filtered off and melted at ≃179° C. The filtrate was concentrated hot to 400 ml, left to crystallize to obtain 55.19 g of 2,3-dihydro-α-[(methylamino)-methyl]-1-benzyl-1H-indol-4-methanol melting at ≃112° C.

Provenance & Evidence