1-[4-[(E)-C-(2,4-dichlorophenyl)-N-hydroxycarbonimidoyl]piperidin-1-yl]ethanone → HCID 66741568, compound

HRID 72851Notes

Reaction equation

HRID 72851 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[C:9](=[N:19]/[OH:20])/[CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]1.CC(C)([O-])C.[K+]>C1COCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([CH:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]3)=[N:19][O:20][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 130764041-[4-[(E)-C-(2,4-dichlorophenyl)-N-hydroxycarbonimidoyl]piperidin-1-yl]ethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 66741568HCID 66741568, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-{(2,4-Dichloro-phenyl)-[(E)-hydroxyimino]-methyl}-piperidin-1-yl)-ethanone (2.15 g, 7 mmol) was solved in THF (34 mL) and potassium tert-butoxide was added (0.844 g, 7.5 mmol). The mixture was stirred for 2 hours until TLC indicated the end of the reaction. The solvent was removed and the mixture purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1). The combined producted fractions were evaporated under reduced pressure to yield 1.45 g of a colourless oil (75%). MS (m/e): 279.1 (M+H+).

Workup

  1. customthe end of the reaction
  2. customThe solvent was removed
  3. customthe mixture purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1)
  4. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e66d41e08544725ac1cf4a983bae41f
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Reaction notes

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