Hydrochloric Acid → HCID 86591238, compound

Participants

Reaction Steps

To a stirred suspension of lithium aluminium hydride (95%; 55 mg, 1.4 mmol) in anhydrous ether (15 mL) under Ar was added (3R,10aS)-7-chloro-1,2,3,4,10,10a-hexahydro-3-methylpyrazino[1,2-a]indole-1,4-dione (82 mg, 0.33 mmol). The mixture was heated at reflux for 18 h, then allowed to cool to ambient tempera . Water (0.06 mL) was added, followed by aqueous NaOH (15% w/v; 0.06 mL) then water (0.18 mL) and magnesium sulfate (2 g) were added. The mixture was filtered and the filter-cake washed with ethyl acetate. The filtrate was concentrated in vacuo and purification by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide (9:1:0)→(90:8:2)] gave a colourless oil which crystallised on standing (53 mg, 74%). The oil was dissolved in acetone (0.5 mL) and treated with ethereal HCl (1M; 0.71 mL, 0.71 mmol) followed by ether (5 mL). The resultant precipitate was filtered, washed with ether and dried to afford the title compound (51 mg, 83%) as a white solid: mp 260° C. (dec); Found C, 55.63; H, 6.28; N, 10.61%. C12H16Cl2N2 requires: C, 55.61; H, 6.22; N, 10.80%.

Provenance & Evidence