Sodium Iodide → HCID 21744304, compound

HRID 1885322Notes

Reaction equation

HRID 1885322 reaction equation
[CH3:1][N:2]([CH2:14][CH2:15][CH2:16][Cl:17])[C:3]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)=[O:4].[F:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[ClH:17].[ClH:17].[CH3:1][N:2]([CH2:14][CH2:15][CH2:16][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][N:25]1[C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([F:18])=[CH:32][CH:31]=1)[C:3]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2737266(4-Fluorophenyl)(piperidin-1-yl)methanoneHCID 19752303HCID 19752303, compound

Product 1

HCID 21744304HCID 21744304, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-methyl-N-(3-chloropropyl)-1,2-benzisothiazole-3-carboxamide (7.13 g), 1-(4-fluorobenzoyl)piperidine (6.44 g), potassium carbonate (7.33 g), and sodium iodide (300 mg) in dry 1-methyl-2-pyrrolidinone (150 ml) was heated to 120° C., with stirring, under nitrogen. After 24 hrs, the mixture was allowed to cool to room temperature and the residue was partitioned between ethyl acetate/water. The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The crude residue was chromatographed twice on silica using 10:90 methanol:ethyl acetate as the eluent. The appropriate fractions were collected and evaporated. The residue was dissolved in ether and hydrogen chloride in ethanol was added Recrystallized of the precipitate from dichloromethane/ether gave 0.642 g (5.09%) of produ mp 189°-191° C.

Workup

  1. temperatureto cool to room temperature
  2. customthe residue was partitioned between ethyl acetate/water
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude residue was chromatographed twice on silica using 10:90 methanol
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. dissolutionThe residue was dissolved in ether
  11. additionhydrogen chloride in ethanol was added
  12. customRecrystallized of the precipitate from dichloromethane/ether
  13. customgave 0.642 g (5.09%) of produ mp 189°-191° C.

Sources & evidence

ORD record
ord-9bdddfa9196444c592bfe5e3d6ab2150
Source dataset
uspto-grants-1992_09
Patent number
US05143923

Reaction notes

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