Water → 3-(1-Piperazinyl)-1,2-benzisothiazole

HRID 339736Notes

Reaction equation

HRID 339736 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][N:9]=1.O>CC(O)(C)C>[N:1]1([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10][N:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 5981903-Chloro-1,2-benzisothiazole

Product 1

HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazole

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of piperazine (10.2 g, 0.118 mmol) and 3-chloro-1,2-benzisothiazole (4.0 g, 0.024 mmol) in t-BuOH (4 mL) was refluxed overnight. The reaction mixture was poured into water (100 mL) and extracted with toluene (200 mL). The organic phase was dried over MgSO4 and evaporated until about 20 mL remained, under vacuum. The resulting suspension was cooled at 0-5° C. overnight. The precipitate was filtered and dried under vacuum to provide 3-(piperazin-1-yl)benzo[d]isothiazole as an intermediate (3.36 g, 15.4 mmol, 65%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with toluene (200 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated until about 20 mL
  5. filtrationThe precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-92b7a1a8a3144fe488139969106a72ca
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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