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

HRID 1585782Notes

Reaction equation

HRID 1585782 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>ClC1C=CC=CC=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

4

Reactant 2

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

Product 1

HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleYield 47.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

304.2 g (3.53 mol) of piperazine, 7.5 g of chlorobenzene, 39.8 g (0.235 mol) of 3-chloro-1,2-benzisothiazole were placed in a four-neck 1000 ml flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, which was heated to stir at about 120° C. for 20 hours. After excess piperazine was removed with water, the reaction mixture was made acidic with hydrochloric acid, extracted into an aqueous layer, which was made alkaline with aqueous sodium hydroxide to obtain 24.4 g (m.p. 89 to 90° C.) of 3-(1-piperazinyl)-1,2-benzisothiazole as crystals. Yield from 3-chloro-1,2-benzisothiazole was 47.4%.

Workup

  1. customequipped with a stirrer
  2. temperaturea thermometer, a dropping funnel and a condenser, which was heated
  3. customAfter excess piperazine was removed with water
  4. extractionextracted into an aqueous layer, which

Sources & evidence

ORD record
ord-1b6d9aaea37f41cabbd16452011ff879
Source dataset
uspto-grants-1999_08
Patent number
US05939548

Reaction notes

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