Hydrogen Peroxide → HCID 69421897, compound

HRID 1349860Notes

Reaction equation

HRID 1349860 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-6cda25ae767c4b279c3665ac3da1a37c
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…