Potassium Hydroxide → HCID 59252270, compound

HRID 2265913Notes

Reaction equation

HRID 2265913 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11](/[C:14](/[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2F)=[N:15]/[OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59252321HCID 59252321, compound

Product 1

HCID 59252270HCID 59252270, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-{(2,5-Difluoro-phenyl)-[(E)-hydroxyimino]-methyl}-piperazine-1-carboxylic acid tert-butyl ester (28.3 g, 82.9 mmol) was suspended in 200 ml dioxane and stirred together with 300 ml 30% KOH in water for 16 hours at reflux. The reaction mixture was cooled and extracted two times with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (95:5 to 40:60) to give 22.7 g (85%) of the product as a white solid. MS (m/e): 322.2 (M−H+).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted two times with dichloromethane
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (95:5 to 40:60)

Sources & evidence

ORD record
ord-b1f1f3dec6344eca95d904404939b098
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

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