Methyl iodide → HCID 66746540, compound

HRID 1019934Notes

Reaction equation

HRID 1019934 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[CH:14][C:15]([S:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[N+:38]([O-:40])=[O:39])(=[O:31])=[O:30])[CH2:24][CH2:23]3)=[N:16]2)=[CH:11][CH:10]=1.CI.C1CCCCC1>CN(C)C=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[CH:14][C:15]([S:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH:25]([N:28]([CH3:1])[S:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[N+:38]([O-:40])=[O:39])(=[O:30])=[O:31])[CH2:26][CH2:27]3)=[N:16]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8078CyclohexaneHCID 10796Cesium carbonateHCID 66746978HCID 66746978, compound

Product 1

HCID 66746540HCID 66746540, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (293 mg, 0.90 mmol, 1.5 eq) is added at room temperature to a stirred solution of N-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-2-nitro-benzenesulfonamide (307 mg, 0.60 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by methyl iodide (56 μL, 0.90 mmol, 1.5 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: cyclohexane:ethyl acetate, 4:1 to 1:0, v/v) to afford N-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-N-methyl-2-nitro-benzenesulfonamide as a yellow solid (106 mg, 34% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-f8700e0344ca49fab7ef2af59f07dbb5
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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