m-Chloroperbenzoic acid → HCID 86702135, compound

HRID 1776191Notes

Reaction equation

HRID 1776191 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH:11]=[CH2:12])(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH:11]1[CH2:12][O:21]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867021342-Ethenyl-1-(methylsulfonyl)piperidine

Product 1

HCID 86702135HCID 86702135, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(methylsulfonyl)-2-vinylpiperidine (0.369 g, 2.0 mmol) in anhydrous methylene chloride (10 mL) was added purified 3-chloroperbenzoic acid (100%, 1.0 g, 6 mmol). The reaction was stirred at room temperature for 65 hours. The reaction mixture was filtered, saturated aqueous sodium sulfite added, and the biphasic solution was stirred for 5 mins. The mixture was diluted with ethyl acetate, and the organic layer successively washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), filtered, and concentrated. The crude product was purified by silica gel column chromatography (30-60% ethyl acetate in hexanes) to give a white semi-solid (0.128 g, 31%). 1H NMR (CDCl3, 300 MHz) δ 3.78-3.74 (br d, 1H, J=13.2 Hz), 3.66-3.61 (m, 1H), 3.37-3.32 (m, 1H), 3.24-3.15 (m, 1H), 2.98 (s, 3H), 2.88-2.85 (dd, 1H, J=4.8, 4.2 Hz), 2.68-2.66 (dd, 1H, J=4.8, 2.6 Hz), 1.81-1.60 (m, 6H). ESI (m/z): 205.9 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionsaturated aqueous sodium sulfite added
  3. stirringthe biphasic solution was stirred for 5 mins
  4. additionThe mixture was diluted with ethyl acetate
  5. washthe organic layer successively washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions
  6. dry with materialdried (anhydrous sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography (30-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-055370e6f1be40898f8a2263275444e3
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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