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

HRID 343588Notes

Reaction equation

HRID 343588 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.ClC1C=CC=CC=1.Cl[C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][N:16]=1>C(O)CO>[N:1]1([C:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:17][N:16]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 7964ChlorobenzeneHCID 5981903-Chloro-1,2-benzisothiazole

Product 1

HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

215.4 g (2.50 mol) of piperazine, 50.0 g of chlorobenzene, 100.0 g of ethylene glycol were placed in a four-neck 1000 ml flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, 169.5 g (1.00 mol) of 3-chloro-1,2-benzisothiazole was added dropwise in the melted state at about 120° C. over 1 hour while stirring, which was thereafter stirred for 2 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 202.4 g (m.p. 89°-90° C.) of 3-(1-piperazinyl)-1,2-benzisothiazole as crystals. Yield from 3-chloro-1,2-benzisothiazole was 92.4%.

Workup

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

Sources & evidence

ORD record
ord-ede2007e863e491c91da20a282468f06
Source dataset
uspto-grants-1999_01
Patent number
US05861511

Reaction notes

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