Sodium Carbonate → HCID 131717513, compound

HRID 483438Notes

Reaction equation

HRID 483438 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)=[O:6].[F:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[OH2:6].[ClH:1].[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[ClH:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2737266(4-Fluorophenyl)(piperidin-1-yl)methanoneHCID 10263700HCID 10263700, compound

Product 1

HCID 131717513HCID 131717513, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-(2-chloroethyl)-1,2-benzisothiazole-3-carboxamide (3.5 g) and 1-(4-fluorobenzoyl)piperidine (3.63 g) in dry 1-methyl-2-pyrrolidinone (125 ml) was heated with stirring to 180° C., under nitrogen. After 3 hr, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium carbonate solution. The aqueous phase was extracted with ethyl acetate, and the combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was triturated with ether, and the filtrate was concentrated. The residue was chromatographed on silica using ethyl acetate as the eluent. The appropriate fractions were combined and concentrated. The residue was taken up in ether and hydrogen chloride in ether was added. The precipitate was recrystallized from methanol/dichloromethane/ether to provide 1.21 g (18.1%) of product, mp 188°-190° C.

Workup

  1. temperaturewas heated
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was triturated with ether
  9. concentrationthe filtrate was concentrated
  10. customThe residue was chromatographed on silica
  11. concentrationconcentrated
  12. additionhydrogen chloride in ether was added
  13. customThe precipitate was recrystallized from methanol/dichloromethane/ether

Sources & evidence

ORD record
ord-8f8c648746d740e08dbd2a12dac81acc
Source dataset
uspto-grants-1993_07
Patent number
US05225412

Reaction notes

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