m-Chloroperbenzoic acid → 3-cyclohexyl-2-methylpyridine N-oxide

HRID 1592415Notes

Reaction equation

HRID 1592415 reaction equation
[CH:1]1([C:7]2[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH:1]1([C:7]2[C:8]([CH3:13])=[N+:9]([O-:22])[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 45098222HCID 45098222, compound

Product 1

HCID 672726033-cyclohexyl-2-methylpyridine N-oxideYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclohexyl-2-methylpyridine (170 mg, 1.0 mmol), in CH2Cl2 (5 mL) was treated with MCPBA (0.33 g, 1.9 mmol) for 18 hours. The solution was then washed with saturated NaHCO3 solution (5 mL), the phases separated, and the aqueous extracted with CH2Cl2 (2×10 mL). The combined organic phases were then dried (Na2SO4), filtered, and concentrated to afford crude 3-cyclohexyl-2-methylpyridine N-oxide as a white solid (0.215 g) which was used immediately in the next reaction.

Workup

  1. washThe solution was then washed with saturated NaHCO3 solution (5 mL)
  2. customthe phases separated
  3. extractionthe aqueous extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic phases were then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f2ae57fe4c34450fb80930496f553237
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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