Hydrogen Peroxide → HCID 69421897, compound

HRID 2183358Notes

Reaction equation

HRID 2183358 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=3)[N:18]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:17]=2)[CH:13]=[CH:14][CH:15]=1.[OH-:33].[Na+].OO>CCO>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([NH2:26])=[O:33])[CH:23]=3)[N:18]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 69422904HCID 69422904, compound

Product 1

HCID 69421897HCID 69421897, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

3-[3-(2-Piperidylethoxy)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.67 g, 1.6 mmol) was dissolved in 2 mL EtOH and the solution was cooled to 0° C. Aqueous 6 N NaOH solution (1.04 mL, 0.25 g, 6.2 mmol) and aqueous 30% H2O2 (0.7 mL, 0.21 g, 6.2 mmol) were added to the reaction mixture. The reaction mixture was warmed to room temperature and stirred for 1.5 h. The reaction was quenched by addition of 6 N HCl. The resultant solution was neutralized by addition of saturated aqueous solution of sodium bicarbonate. The solution was extracted with EtOAc, the organic layer was washed with water, brine, dried (Na2SO4) and filtered. The filtrate was concentrated to 0.61 g (87%) of the title compound obtained as a yellow solid. ES-MS (m/z) 449 [M+H]+.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe reaction was quenched by addition of 6 N HCl
  3. additionThe resultant solution was neutralized by addition of saturated aqueous solution of sodium bicarbonate
  4. extractionThe solution was extracted with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated to 0.61 g (87%) of the title compound
  9. customobtained as a yellow solid

Sources & evidence

ORD record
ord-73b04b4b8d464f06a9101da9c1d3a1e9
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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