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

HRID 913268Notes

Reaction equation

HRID 913268 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>>[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

3

Reactant 2

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

Product 1

HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleYield 24%

Conditions

Temperature
125 °C

Procedure

A mixture of anhydrous piperazine (2.75 g, 32 mmol) and 3-chloro-benzo[d]isothiazole (1.00 g, 5.80 mmol) were heated in a sealed tube in an oil bath at 125° C. for 24 hours. The orange melt was then quenched with ice water and 50% NaOH was added in one portion. The mixture was extracted with dichloromethane to get the crude product which was purified by recrystallization to afford the title compound as a pale yellow solid in 24% yield (0.260 g). MS (ES+) m/z 220 (M+1).

Workup

  1. customThe orange melt was then quenched with ice water and 50% NaOH
  2. additionwas added in one portion
  3. extractionThe mixture was extracted with dichloromethane
  4. customto get the crude product which
  5. customwas purified by recrystallization

Sources & evidence

ORD record
ord-eb8ecdb11ef64b73869bc5fc8e4a7b71
Source dataset
uspto-grants-2011_09
Patent number
US08026360B2

Reaction notes

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