Potassium Carbonate → 3-{4-[2-(4-Nitro-phenyl)-ethyl]-piperazin-1-YL}-1,2-benzisothiazole

HRID 2211857Notes

Reaction equation

HRID 2211857 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[N:8]1([C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][N:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.S(C1C=CC(C)=CC=1)(O[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)(=O)=O>CC(C)=O.C1OCCOCCOCCOCCOCCOC1>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH2:27][N:11]2[CH2:12][CH2:13][N:8]([C:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[S:16][N:15]=3)[CH2:9][CH2:10]2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2447744-Nitrophenethyl tosylateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 219632673-{4-[2-(4-Nitro-phenyl)-ethyl]-piperazin-1-YL}-1,2-benzisothiazoleYield 86.7%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolvent

Procedure

Excess dried, −325 mesh potassium carbonate (20 g) was diluted in 500 mL acetone and 3-piperazin-1-yl-benzoisothiazole hydrochloride (13.05 g, 51.2 mmol) was added. The mixture was stirred for 15 min before 4-nitrophenethyl tosylate (14.93 g, 46.5 mmol) and catalytic 18-crown-6 (0.5 g, 1.9 mmol) was added. The mixture was stirred at reflux for 42 h. After cooling, the salts were filtered off and washed with acetone and the filtrate was concentrated. The residue was taken up in methylene chloride and washed with water. The organic layer was dried over sodium sulfate, and concentrated. The residue was triturated with ethyl acetate and the collected solid was washed with ethyl ether and dried in vacuo to afford 14.86 g of a bright yellow solid. Yield 84%; mp 99° C.; MS (APCI): 369 [M+H]+.

Workup

  1. additionwas added
  2. temperatureat reflux for 42 h
  3. temperatureAfter cooling
  4. filtrationthe salts were filtered off
  5. washwashed with acetone
  6. concentrationthe filtrate was concentrated
  7. washwashed with water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was triturated with ethyl acetate
  11. washthe collected solid was washed with ethyl ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-372a987f120e4e6ba551a73042d498a9
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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