Triacetoxyperiodinane → 1-(4-Nitrophenyl)piperidin-4-one

HRID 2189265Notes

Reaction equation

HRID 2189265 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 6137681-(4-Nitrophenyl)-4-piperidinol

Product 1

HCID 38425621-(4-Nitrophenyl)piperidin-4-oneYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-Nitro-phenyl)-piperidin-4-ol (100 mg, 0.45 mmol) in CH2Cl2 (2 mL) is added Dess-Martin periodinane (286 mg, 0.675 mmol) at for 2.5 hours. The reaction is quenched with 1N NaOH aqueous solution. The aqueous layer is extracted with CH2Cl2, and the organic extracts are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, EtOAc:Hexane=12:88 to 100:0) to give 84 mg of the title compound as a white solid.

Workup

  1. customThe reaction is quenched with 1N NaOH aqueous solution
  2. extractionThe aqueous layer is extracted with CH2Cl2
  3. dry with materialthe organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (SiO2, EtOAc:Hexane=12:88 to 100:0)

Sources & evidence

ORD record
ord-c60dbcfcb3494f289e0243c61e34bb6f
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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