Sodium Iodide → HCID 19752325, compound

HRID 1885309Notes

Reaction equation

HRID 1885309 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)=[O:7].Cl.[Cl:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:24][O:25][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[ClH:1].[Cl:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([N:26]3[CH2:27][CH2:28][CH:29]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]4[C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=5[S:10][N:9]=4)=[O:7])[CH2:30][CH2:31]3)=[N:24][O:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10332575HCID 10332575, compoundHCID 19752293HCID 19752293, compound

Product 1

HCID 19752325HCID 19752325, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-(3-chloropropyl)-1,2-benzisothiazole-3-carboxamide (5.0 g), 1-(6-chloro-1,2-benzisoxazol-3-yl)piperidine hydrochloride (5.40 g), potassium carbonate (5.40 g), and sodium iodide (100 mg) in dry N-methylpyrrolidinone (100 ml), was heated to 180° C., with stirring, under nitrogen. After 36 hr, the reaction mixture was allowed to cool to room temperature and partitioned between ethyl acetate/water. The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on silica using ethyl acetate as the eluent. The appropriate fractions were collected and concentrated. The filtrate was treated with hydrogen chloride in ether. The salt was recrystallized from methanol/dichloromethane/ether to provide 2.87 g (29.4%) of product, mp 221°-223° C.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned 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 concentrated in vacuo
  7. customThe residue was chromatographed on silica
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. additionThe filtrate was treated with hydrogen chloride in ether
  11. customThe salt was recrystallized from methanol/dichloromethane/ether

Sources & evidence

ORD record
ord-76b98de7bb174ffdae9ea4f9fc59e4f2
Source dataset
uspto-grants-1992_09
Patent number
US05143923

Reaction notes

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