Pyridine → 1-(5-Methyl-4-phenyl-4H-1,2,4-triazol-3-yl)piperazine

HRID 1682352Notes

Reaction equation

HRID 1682352 reaction equation
Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]([CH3:13])=[N:4][N:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.N1C=CC=CC=1>CO.C(Cl)Cl>[CH3:13][C:5]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 4837PiperazineHCID 12217059HCID 12217059, compound

Product 1

HCID 224187621-(5-Methyl-4-phenyl-4H-1,2,4-triazol-3-yl)piperazine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3-bromo-5-methyl-4-phenyl-4H-1,2,4-triazole (4.16 g), 15.07 g of piperazine and 20 ml of pyridine is stirred at 100° under nitrogen for 22 h. The reaction is monitored by TLC (8% methanol/methylene chloride) and after this period of time no change occurs. The mixture is subsequently placed in a Parr bomb and heated in an oil bath at 180° for 24 h. Bomb pressure increased by 40 psi. The mixture is worked up by partitioning between chloroform and water. The organic phase is washed with saturated aqueous sodium bicarbonate (2×) and with saline (2×), dried over sodium sulfate and concentrated to a solid, the product is recrystallized in ethyl acetate, MS [M+H]+ 243.1484

Workup

  1. temperatureheated in an oil bath at 180° for 24 h
  2. temperatureincreased by 40 psi
  3. customby partitioning between chloroform and water
  4. washThe organic phase is washed with saturated aqueous sodium bicarbonate (2×) and with saline (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customthe product is recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-d5d1bb579d8746f0a4c09ea06f97ed93
Source dataset
uspto-grants-1992_12
Patent number
US05175281

Reaction notes

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