Sodium Iodide → 2-(Iodomethyl)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidine

HRID 1643459Notes

Reaction equation

CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=1[CH3:25])(=[O:15])=[O:14])(=O)=O.[I-:26].[Na+]>CC(C)=O>[I:26][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=1[CH3:25])(=[O:15])=[O:14]

Participants

Conditions

Temperature: 120 °C

Procedure

(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methyl methanesulfonate (0.25 g, 0.639 mmol) and sodium iodide (0.383 g, 2.554 mmol) were dissolved in acetone (7 ml) and the solution was heated at 120° C. in a microwave oven (CEM Discover; 100 watt) for 1 h. The solvent was removed in vacuo, the residue was dissolved in sodium thiosulfate solution (20 ml, 5 mmol/l) and diethyl ether (40 ml), the phases were separated and the aqueous phase was extracted with diethyl ether (2×20 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether/methylene chloride (3:1:1). Yield: 0.2 g (74%)

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in sodium thiosulfate solution (20 ml, 5 mmol/l)
customdiethyl ether (40 ml), the phases were separated
extractionthe aqueous phase was extracted with diethyl ether (2×20 ml)
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (silica gel) with hexane/diethyl ether/methylene chloride (3:1:1)

Sources & evidence

ORD record: ord-2a1884578f16492d8121004acff74295
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119805B2

Reaction notes

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