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

HRID 916204Notes

Reaction equation

HRID 916204 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-2b9b46eb1eb94704be1678ef35c15da9
Source dataset
uspto-grants-2007_09
Patent number
US07268146B2

Reaction notes

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