Methyl iodide → HCID 69412215, compound

HRID 1592740Notes

Reaction equation

HRID 1592740 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:28]I>C1COCC1.CCOCC>[C:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][N:23]([S:24]([CH3:27])(=[O:26])=[O:25])[CH3:28])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 542677021,1-Dimethylethyl 4-[2-[[(methylsulfonyl)amino]methyl]phenyl]-1-piperazinecarboxylate

Product 1

HCID 69412215HCID 69412215, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% in oil, 113 mg, 2.82 mmol) in THF (20 mL) at 0° C. under nitrogen was added a solution of 1-Boc-4-[2-(methanesulfonylamino-methyl)-phenyl]-piperazine (0.99 g, 2.68 mmol) in THF (5 mL). The mixture was stirred for about 1 hour at room temperature. It then was cooled back to 0° C. and treated with methyl iodide (0.184 mL, 2.95 mmol). After stirring for about 20 hours, the reaction mixture was diluted with ether (150 mL) and then quenched by addition of saturated aqueous ammonium chloride (50 mL). The organic phase was separated, washed with water (50 mL) and brine (50 mL) and then dried over magnesium sulfate. Concentration under reduced pressure followed by silica gel chromatography (30% ethyl acetate in hexanes) afforded the title compound (0.96 g, 94%) as a clear oil.

Workup

  1. temperatureIt then was cooled back to 0° C.
  2. stirringAfter stirring for about 20 hours
  3. customquenched by addition of saturated aqueous ammonium chloride (50 mL)
  4. customThe organic phase was separated
  5. washwashed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c8ddaf2cc67c4e83a2ca9d861e91b025
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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