1-(2-Methoxyphenyl)piperazine → HCID 19752298, compound

HRID 483432Notes

Reaction equation

HRID 483432 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].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[ClH:1].[ClH:1].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10][N:9]=2)=[O:7])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10332575HCID 10332575, compound

Product 1

HCID 19752298HCID 19752298, compoundYield 53.2%

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 (4.2 g), 1-(2-methoxyphenyl)piperazine (3.3 g), potassium carbonate (4.55 g), and sodium iodide (100 mg) in dry N-methylpyrrolidinone (150 ml) was heated to 180° C., with stirring, under nitrogen. After 24 hr, the reaction mixture was allowed to cool to room temperature and partitioned between ether/water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica using ether as the eluent. The appropriate fractions were collected and evaporated. The residue was taken up in ether and hydrogen chloride in ether was added. Recrystallization of the precipitate from methanol/dichloromethane/ether provided 2.12 g (26.6%) of product, mp 191°-194° C.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between ether/water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was chromatographed on silica
  7. customThe appropriate fractions were collected
  8. customevaporated
  9. additionhydrogen chloride in ether was added
  10. customRecrystallization of the precipitate from methanol/dichloromethane/ether

Sources & evidence

ORD record
ord-153a2aefdb9a4a4c9e4b76f1cddd3331
Source dataset
uspto-grants-1993_07
Patent number
US05225412

Reaction notes

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