Acetic Anhydride → 1-Acetyl-4-(4-fluorobenzoyl)piperidine

HRID 926515Notes

Reaction equation

HRID 926515 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([CH:17]2[CH2:22][CH2:21][N:20]([C:5](=[O:7])[CH3:6])[CH2:19][CH2:18]2)=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (2.32 g, 24.6 mmol) was added dropwise to a cold (0° C.) solution of (4-fluorophenyl)(piperidin-4-yl)methanone (5.00 g, 20.5 mmol) in DCM (33 mL) and triethylamine (10.0 mL, 71.8 mmol). The resulting mixture was removed from the ice bath after 5 minutes and stirred at room temperature for 2 hours. The reaction was then added to a mixture of 1 M aqueous K3PO4 (100 mL), H2O, and DCM. The layers were separated and the aqueous layer again extracted with DCM. The combined organic layers were dried (Na2SO4), filtered, concentrated under reduced pressure and chromatographed (DCM/EtOAc) to provide the title compound as a clear oil.

Workup

  1. customThe resulting mixture was removed from the ice bath after 5 minutes
  2. additionThe reaction was then added to a mixture of 1 M aqueous K3PO4 (100 mL), H2O, and DCM
  3. customThe layers were separated
  4. extractionthe aqueous layer again extracted with DCM
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed (DCM/EtOAc)

Sources & evidence

ORD record
ord-b5c26ba8094a4d36858e5d9c3ad1f340
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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