Methyl iodide → 1-(4-Benzenesulfonyl-4-methylpentyl)-3-methoxypiperidine

HRID 2212094Notes

Reaction equation

HRID 2212094 reaction equation
[C:1]1([S:7]([C:10]([CH3:22])([CH3:21])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([OH:20])[CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23]I.[H-].[Na+]>O1CCCC1>[C:1]1([S:7]([C:10]([CH3:22])([CH3:21])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([O:20][CH3:23])[CH2:15]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 696627361-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine

Product 1

HCID 696632391-(4-Benzenesulfonyl-4-methylpentyl)-3-methoxypiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine (0.1 g, 0.31 mmol), methyl iodide (22 μL, 0.35 mmol) and sodium hydride (60% dispersion in mineral oil, 15 mg, 0.35 mmol) were combined in tetrahydrofuran (2 ml) and stirred at room temperature for 18 hours. The reaction was quenched by the addition of water and brine and the mixture extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2–5% methanol/dichloromethane, to give the title compound. The hydrochloride salt was obtained by treatment with ethereal hydrogen chloride and crystallisation from ethanol/diethyl ether (77 mg, 74%). NMR of hydrochloride salt:

Workup

  1. customThe reaction was quenched by the addition of water and brine
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with 2–5% methanol/dichloromethane

Sources & evidence

ORD record
ord-24cbdc85ef5f4a85ab10759b3fd84b5a
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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