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

HRID 1585783Notes

Reaction equation

HRID 1585783 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]Cl)#[N:8]>ClC1C=CC=CC=1>[N:1]1([C:7]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 110083382-cyanobenzenesulfenyl chloride

Product 1

HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleYield 74.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

86.2 g (1.00 mol) of piperazine and 7.5 g of chlorobenzene were placed in a four-neck 500 ml flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, 53.5 g (0.25 mol) of 2-cyanobenzenesulfenyl chloride was added dropwise in the melted state at about 130° C. over 1 hour while stirring, which was thereafter stirred for 4 hours to complete the reaction. 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 40.9 g (m.p. 89 to 90° C.) of 3-(1-piperazinyl)-1,2-benzisothiazole as crystals. Yield from 2-cyanobenzenesulfenyl chloride was 74.7%.

Workup

  1. customequipped with a stirrer
  2. stirringwhich was thereafter stirred for 4 hours
  3. customthe reaction
  4. customAfter excess piperazine was removed with water
  5. extractionextracted into an aqueous layer, which

Sources & evidence

ORD record
ord-05397dc113904c87af7cbb0e53e91de4
Source dataset
uspto-grants-1999_08
Patent number
US05939548

Reaction notes

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