Hydrochloric Acid → HCID 86591240, compound

To a stirred suspension of lithium aluminium hydride (95%; 55 mg, 1.4 mmol) in anhydrous ether (15 mL) under Ar was added (3S,10aR) 7-chloro-1,2,3,4,10,10a-hexahydro-3-methylpyrazino[1,2-a]indole-1,4-dione (83 mg, 0.33 mmol). The mixture was heated at reflux for 18 h, then allowed to cool to ambient temperature. 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) was 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 (68 mg, 92%). The oil was dissolved in acetone (0.5 mL) and treated with ethereal HCl (1M; 0.81 mL, 0.81 mmol) followed by ether (5 mL). The resultant precipitate was filtered, washed with ether and dried to afford the title compound (62 mg, 78%) as a white solid: mp 265° C. (dec); Found C, 55.66; H, 62.8; N, 10.72%. C12H16Cl2N2 requires: C, 55.61; H, 6.22; N, 10.80%.

1. temperatureThe mixture was heated
2. temperatureat reflux for 18 h
3. filtrationThe mixture was filtered
4. washthe filter-cake washed with ethyl acetate
5. concentrationThe filtrate was concentrated in vacuo and purification by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide (9:1:0)→(90:8:2)]
6. customgave a colourless oil which
7. customcrystallised
8. dissolutionThe oil was dissolved in acetone (0.5 mL)
9. filtrationThe resultant precipitate was filtered
10. washwashed with ether
11. customdried

ORD record

ord-60482caf5f0e4541bd5f46e86d6eb7e9

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800627B1