Piperazine → 6-Chloro-2-(piperazin-1-yl)-1,3-benzothiazole

HRID 132932

Reaction equation

HRID 132932 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CN(C=O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 771762,6-Dichlorobenzothiazole

Product 1

HCID 27465956-Chloro-2-(piperazin-1-yl)-1,3-benzothiazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.07 g (5.24 mmol) of 2,6-dichlorobenzothiazole in dry DMF (25 mL) was added 2.4 g of potassium carbonate (15.7 mmol) and 0.5 g of piperazine (5.8 mmol). The mixture was stirred at room temperature for 4 h. When the reaction was complete it was partitioned between EtOAc (150 mL) and water (50 mL) and separated. The aqueous layer was extracted with EtOAC (2×100 mL). The combined organic layers were then washed with water (2×25 mL), brine, dried over Na2SO4, and the solvent was removed under reduced pressure to give 1.33 g (100%) of desired product as a white solid. MS (electrospray): exact mass calculated for C11H12CIN3S, 253.04; m/z found, 254.0 [M+H]+.

Workup

  1. customwas partitioned between EtOAc (150 mL) and water (50 mL)
  2. customseparated
  3. extractionThe aqueous layer was extracted with EtOAC (2×100 mL)
  4. washThe combined organic layers were then washed with water (2×25 mL), brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-194561370f28496e95436e2998a266d2
Source dataset
uspto-grants-2008_06
Patent number
US07388011B2

Linked notes

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