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

HRID 2209885Notes

Reaction equation

HRID 2209885 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 increases 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. temperatureincreases 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-4cf4c610846b4845838b55181946cfb5
Source dataset
uspto-grants-1995_10
Patent number
USRE035053

Reaction notes

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