Potassium sodium tartarate → HCID 9883089, compound

Participants

Reaction Steps

A suspension of the 3-(2-amino-1,2-dioxoethyl)-5-(4-phenylbutyloxy)indole (0.4 g, 1.3 mmol) and LiAIH4 (0.32 g, 8.44 mmol) in dry THF (30 ml) was heated at reflux for 3 days under nitrogen. After allowing the reaction mixture to cool to room temperature, the excess LiAIH4 was decomposed by the addition of a saturated solution of sodium potassium tartrate (3 ml) at 0° C. The precipitated material was removed by filtration and the flitrate was dried (MgSO4). The solvent was removed under reduced pressure to afford an oily product. The oil was purified by column chromatography using a solvent system of CH2Cl2/MeOH (90:10) to provide 3-(2-aminoethyl)-5-(4-phenylbutyloxy)indole (32.8% yield) as an oil. The oil was taken up in anhydrous Et2O (5 ml) and added to a saturated ethereal solution of oxalic acid. The resultant oxalate salt was collected by filtration, washed with anhydrous Et2O (2×10 ml), and recrystallized from MeOH/Et2O to afford a tan solid; mp 130°-132° C. Analytically calculated formula C20H24N2O. (COOH)2.

Provenance & Evidence