Methyl iodide → HCID 69417821, compound

HRID 456465Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[C:33](OCC)(=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([N:24]([S:25]([CH3:28])(=[O:27])=[O:26])[CH3:33])[CH3:23])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(2-Methanesulfonylamino-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (470 mg, 1.14 mmol) was dissolved in THF (20 mL) and cooled to 0° C. Sodium hydride (29 mg of 60% dispersion in oil, 1.2 mmol) was added followed by dropwise addition of methyl iodide (78 μL, 1.25 mmol). The mixture was warmed to r.t. and stirred for about 36 hours. Ethyl acetate (20 mL) was added, and the solution was washed with saturated NaHCO3 (5 mL), H2O (5 mL) and brine (5 mL) and then dried over magnesium sulfate. The solvents were removed under reduced pressure to afford the final compound as a clear oil (486 mg, 100%).

Workup

temperatureThe mixture was warmed to r.t.
washthe solution was washed with saturated NaHCO3 (5 mL), H2O (5 mL) and brine (5 mL)
dry with materialdried over magnesium sulfate
customThe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-1af43679bfc84733b5d3cc22ff9c2a6f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186715B2

Reaction notes

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