Potassium Carbonate → HCID 66718352, compound

HRID 2096670Notes

Reaction equation

HRID 2096670 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:22])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70297m-Chloroperbenzoic acidHCID 10583661HCID 10583661, compound

Product 1

HCID 66718352HCID 66718352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-hydroxytetrahydropyran-4-yl)pyridine (2.08 g, 11.6 mmol) in dichloromethane (100 mL) was added, with stirring, m-CPBA (77%, 2.86 g, 12.76 mmol) and the mixture stirred at ambient temperature overnight. After this time, potassium carbonate (1.62 g, 11.60 mmol) was added, the reaction stirred for two hours and the mixture filtered. A further aliquot of potassium carbonate (1.62 g, 11.60 mmol) was added to the filtrate and the mixture again stirred for two hours. After filtration and concentration in vacuo, the N-oxide was obtained as a pale brown solid (2.28 g, quant.) and used without further purification; NMR δH (400 MHz, DMSO) 8.33 (1H, dd, J 6.3 Hz, 1.1 Hz), 7.65 (1H, dd, J 8.0 Hz, 2.0 Hz), 7.52 (1H, td, J 7.9 Hz, 1.3 Hz), 7.44 (1H, td, J 7.6 Hz, 2.0 Hz), 7.32 (1H, br s), 3.78 (4H, m), 2.23 (2H, td, J 12.5 Hz, 5.1 Hz), 1.80 (1H, d, J 11.4 Hz); LC-MS Retention time 0.99 min, (M+H)+ 196.

Workup

  1. stirringthe reaction stirred for two hours
  2. filtrationthe mixture filtered
  3. stirringthe mixture again stirred for two hours
  4. filtrationAfter filtration and concentration in vacuo

Sources & evidence

ORD record
ord-ec7de1a7bdd04e7bae87bb3f7b7728da
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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