Acetic Anhydride → 1-Acetyl-4-benzoylpiperidine

HRID 627496

Reaction equation

HRID 627496 reaction equation
Cl.[C:2]1([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17](OC(C)=O)=[O:18]>C(Cl)Cl>[C:8]([CH:10]1[CH2:15][CH2:14][N:13]([C:17](=[O:18])[CH3:16])[CH2:12][CH2:11]1)(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27244374-Benzoylpiperidine hydrochloride

Product 1

HCID 27407141-Acetyl-4-benzoylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of phenyl(piperidin-4-yl)methanone hydrochloride (743 mg, 3.29 mmol, Apollo Scientific) in DCM (13.2 mL) and TEA (1.10 mL, 7.90 mmol) was treated with Ac2O (0.373 mL, 3.95 mmol) dropwise over 1 min on an ice bath under argon, and the resulting translucent mixture was immediately removed from the ice bath and stirred at room temperature overnight. The reaction was then partitioned with 1 M HCl (1×8 mL) and 1 M NaOH (1×8 mL), and the organic layer was dried (Na2SO4), filtered, and concentrated to provide the title compound as a translucent beige oil that crystallized upon standing.

Workup

  1. customthe resulting translucent mixture was immediately removed from the ice bath
  2. customThe reaction was then partitioned with 1 M HCl (1×8 mL) and 1 M NaOH (1×8 mL)
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e76c6bd2a5040c4997c089712112ea1
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Linked notes

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