Piperazine → 1-[3-(4-Methylphenyl)-1,2,4-thiadiazol-5-yl]piperazine

HRID 570563Notes

Reaction equation

HRID 570563 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[N:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CCO>[C:10]1([CH3:13])[CH:11]=[CH:12][C:7]([C:4]2[N:3]=[C:2]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[S:6][N:5]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 226110665-Chloro-3-p-tolyl-[1,2,4]thiadiazole

Product 1

HCID 577122581-[3-(4-Methylphenyl)-1,2,4-thiadiazol-5-yl]piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chloro-3-p-tolyl-1,2,4-thiadiazole (900 mg, 4.27 mmol) and piperazine (1.84 g, 21.4 mmol) in 25 mL EtOH were heated to reflux and stirred for 1 h at this temperature. The resulting yellow solution was cooled to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography on silica eluting with a gradient formed from DCM, MeOH and NEt3 to yield after evaporation of the product containing fractions 1.1 g (99%) of the title compound as light yellow solid. MS (m/e): 261.3 (MH+).

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica eluting with a gradient
  5. customformed from DCM, MeOH and NEt3
  6. customto yield
  7. customafter evaporation of the product
  8. additioncontaining fractions 1.1 g (99%) of the title compound as light yellow solid

Sources & evidence

ORD record
ord-9fe83ad1164b457095a0afb5f3d5d9e5
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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