Hydrochloric Acid → HCID 86591238, compound

HRID 392091Notes

Reaction equation

HRID 392091 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[C:20](=O)[NH:19][C@H:18]([CH3:22])[C:17](=O)[N:14]3[C:15]=2[CH:16]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2].Cl>CCOCC.O>[ClH:7].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[CH2:20][NH:19][C@H:18]([CH3:22])[CH2:17][N:14]3[C:15]=2[CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 69606907HCID 69606907, compound

Product 1

HCID 86591238HCID 86591238, compoundYield 119.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-93c8dd87cb46497b83d92b8ae443eca9
Source dataset
uspto-grants-2004_10
Patent number
US06800627B1

Reaction notes

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