Sodium Carbonate → HCID 67156646, compound

HRID 549129Notes

Reaction equation

HRID 549129 reaction equation
[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=[CH:10][C:9]=3[N:18]=[C:6]2[CH2:5][N:4]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N+:11]([O-:31])=[CH:10][C:9]=3[N:18]=[C:6]2[CH2:5][N:4]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67156821HCID 67156821, compound

Product 1

HCID 67156646HCID 67156646, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(11S)-11-Methyl-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline (1.01 g, 3.19 mmol) was dissolved in dichloromethane (40 mL) and treated with MCPBA (0.94 g, 77% max). After stirring overnight, the reaction was treated with 20 mL of 2% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with dichloromethane (10×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give (11S)-11-methyl-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline 5-oxide (1.06 g) as a tan solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with dichloromethane (10×10 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5848978158514a639ecaad2a1381e07c
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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