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

HRID 241592Notes

Reaction equation

HRID 241592 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[OH-].[Na+]>>[CH2:13]1[NH:14][CH2:15][CH2:16][N:11]([C:2]2[C:6]3[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=3)[S:4][N:3]=2)[CH2:12]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 5981903-Chloro-1,2-benzisothiazole

Product 1

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

Conditions

Temperature
125 °C

Procedure

3-chloro-(1,2-benzisothiazole) (14 g, 200 mmol) and anhydrous piperazine (6.8 g, 40 mmol) are placed in an egg type flask and heated at 125° C. for 24 hours. After completion of reaction, 52 ml of an ice-water mixture is added for quenching the reaction. The mixture is further added with 3.2 g of 50% NaOH solution, stirred 5 minutes and extracted with CH2Cl2 (50 ml×3). The organic layer is washed with an ice-water mixture (50 ml×2) and saturated saline (50 ml×2), and dried over anhydrous MgSO4 to obtain 4-(1,2-benzisothiazol-3-yl)-1-piperazine.

Workup

  1. additionis added
  2. customfor quenching
  3. customthe reaction
  4. extractionextracted with CH2Cl2 (50 ml×3)
  5. washThe organic layer is washed with an ice-water mixture (50 ml×2) and saturated saline (50 ml×2)
  6. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-ca76e14302c14f7ba0763a1529c3d3e7
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

Loading…