Acetic Acid → N-(2-Cyano-4-fluorophenyl)-4-piperidone

HRID 842788Notes

Reaction equation

HRID 842788 reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[C:18]#[N:19])[CH2:7][CH2:6]2)[O:4]C1C.C(O)(=O)C>Cl>[C:18]([C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)#[N:19]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86757964N-(2-Cyano-4-fluorophenyl)-4-piperidone propylene ketal

Product 1

HCID 22615446N-(2-Cyano-4-fluorophenyl)-4-piperidone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 39 (1.483 g, 5.36 mmol) in 6N aqueous HCl (25 mL) was treated with acetic acid (50 mL) at room temperature. The mixture was stirred at room temperature (3 d). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with three additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 20% EtOAc-80% hexane) afforded the title compound (40).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with three additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8155b2e79d0547bb9a4ca76691dbe986
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…