Acetic Anhydride → 1-(4-(4-bromo-1H-pyrazol-1-yl)piperidin-1-yl)ethanone

HRID 2400331Notes

Reaction equation

HRID 2400331 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 534078484-(4-bromo-1H-pyrazol-1-yl)piperidine hydrochloride

Product 1

HCID 593926411-(4-(4-bromo-1H-pyrazol-1-yl)piperidin-1-yl)ethanoneYield 81.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(4-bromopyrazol-1-yl)piperidine hydrochloride (300 mg, 1.13 mmol) in pyridine (3 ml) was added acetic anhydride (0.107 ml, 1.13 mmol) under an inert atmosphere. The reaction was stirred at 40° C., until reaction complete then evaporated under reduced pressure and re-evaporated with toluene twice, then partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the product (250 mg), which was used without further purification MS: [M+H]+=272

Workup

  1. customevaporated under reduced pressure
  2. customre-evaporated with toluene twice
  3. custompartitioned between water and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cc8b5081cb04140b2a1104b5bc99375
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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