Hydrogen Peroxide → HCID 131709887, compound

HRID 918341Notes

Reaction equation

HRID 918341 reaction equation
[C:1]([CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:8]=2[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].OO.[Mn]([O-])(=O)(=O)=[O:28].[K+]>CO.O>[C:1]([CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:18][CH2:19][N+:20]3([O-:28])[CH2:21][CH2:22][CH2:23][CH2:24]3)[C:8]=2[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 516875Potassium PermanganateHCID 13584819HCID 13584819, compound

Product 1

HCID 131709887HCID 131709887, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product of Example 1 as free base (22.25g) in methanol (300 ml) was cooled to 0° (ice/water bath). Aqueous 30% w/v hydrogen peroxide (31.4g) was added dropwise over about 15 minutes, with cooling and stirring. The mixture was kept at ambient temperature for three days, and the excess hydrogen peroxide was then decomposed with a trace of potassium permanganate. The mixture was evaporated to dryness and the residue was dissolved in hot isopropanol (40 ml). Water (500 ml) was added with stirring and the mixture was refrigerated overnight, yielding a precipitate which was dissolved in hot water, filtered, and cooled, yielding a precipitate of 14.5g of 1-[2-(3-tert-butyl-1,2,3,4-tetrahydrocarbazole-9-yl) ethyl]pyrrolidine-N-oxide quarter-hydrate, m.p. 163°-5°C.

Workup

  1. additionwas added dropwise over about 15 minutes
  2. temperaturewith cooling
  3. customThe mixture was evaporated to dryness
  4. dissolutionthe residue was dissolved in hot isopropanol (40 ml)
  5. additionWater (500 ml) was added
  6. stirringwith stirring
  7. waitthe mixture was refrigerated overnight
  8. customyielding a precipitate which
  9. filtrationfiltered
  10. temperaturecooled

Sources & evidence

ORD record
ord-49e416c544504bfd857cb103a489a423
Source dataset
uspto-grants-1976_07
Patent number
US03970757

Reaction notes

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