Sodium Iodide → 1-(2-Chloro-4,6-dimethylphenyl)piperidin-2-one

HRID 2113777Notes

Reaction equation

HRID 2113777 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15]Cl.CC(C)([O-])C.[K+].[I-].[Na+]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 121439375-Chloropentanoic acid (2-chloro-4,6-dimethylphenyl)amideHCID 23665647Potassium tert-butoxide

Product 1

HCID 121439381-(2-Chloro-4,6-dimethylphenyl)piperidin-2-oneYield 100.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

5-Chloropentanoic acid (2-chloro-4,6-dimethylphenyl)amide (21.7 g), potassium t-butoxide (9.34 g), and sodium iodide (1.2 g) were combined in 200 mL t-butanol and the mixture was stirred in a 60° C. oil bath for 3 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with additional ethyl acetate. The organic phases were washed with brine, dried with magnesium sulfate, and concentrated to give 18.9 g of 1-(2-chloro-4,6-dimethylphenyl)piperidin-2-one as a solid: mp 107.7-108.7° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe aqueous phase was washed with additional ethyl acetate
  4. washThe organic phases were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f56dd91abe854f168435f71ef4d1ac5f
Source dataset
uspto-grants-2008_10
Patent number
US07432283B2

Reaction notes

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