Potassium Iodide → HCID 19786609, compound

HRID 1196595Notes

Reaction equation

HRID 1196595 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:19](=[O:20])[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])=[N:10][O:11][C:7]=2[CH2:6][CH2:5]1.[C:21](=[O:24])([O-])[O-:22].[K+].[K+].C(N(C(C)C)CC)(C)C.[F:36][C:37]1[CH:50]=[CH:49][C:40]([C:41]([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[O:42])=[CH:39][CH:38]=1.[I-].[K+]>CN(C=O)C>[C:21]([OH:22])(=[O:24])[C:6]1[C:7](=[CH:8][CH:19]=[CH:4][CH:5]=1)[OH:11].[F:36][C:37]1[CH:38]=[CH:39][C:40]([C:41]([CH:43]2[CH2:48][CH2:47][N:46]([CH2:2][CH2:3][CH:4]3[C:19](=[O:20])[C:8]4[C:9]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=5[F:18])=[N:10][O:11][C:7]=4[CH2:6][CH2:5]3)[CH2:45][CH2:44]2)=[O:42])=[CH:49][CH:50]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 19786538HCID 19786538, compound

Product 1

HCID 19786609HCID 19786609, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution consisting of 5-(2-chloroethyl)-3-(2-fluorophenyl)-6,7-dihydro-1,2-benzisoxazol-4(5H)-one (2.5 g) and DMF (85 ml) was added anhydrous potassium carbonate (0.6 g), diisopropylethyl amine (2.2 ml), 4-(4-fluorobenzoyl)piperidine (2.3 g) and potassium iodide (70 mg) at room temperature with stirring. The flask was flushed with nitrogen and warmed to 80° C. for 19 hours. Upon cooling to room temperature, water and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude product.

Workup

  1. customThe flask was flushed with nitrogen
  2. temperatureUpon cooling to room temperature
  3. additionwater and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted 3 times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d81db9e13bc749d78e8d43e6757535cf
Source dataset
uspto-grants-1992_05
Patent number
US05114936

Reaction notes

Loading…