1H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]- → 3-(4-[4-Aminophenyl]-cis-2,5-dimethylpiperazin-1-yl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 476565Notes

Reaction equation

HRID 476565 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][C@H:14]([CH3:16])[NH:13][CH2:12][C@@H:11]2[CH3:17])=[CH:6][CH:5]=1)([O-])=O.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26]1([CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)[CH2:28][O:27]1>C(O)CCCC>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C@@H:11]([CH3:17])[CH2:12][N:13]([CH2:28][C:26]([C:20]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=3[Cl:18])([OH:27])[CH2:29][N:30]3[CH:34]=[N:33][CH:32]=[N:31]3)[C@@H:14]([CH3:16])[CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-HCID 703830304-Nitrophenyl-cis-2,5-dimethylpiperazine

Product 1

HCID 703826873-(4-[4-Aminophenyl]-cis-2,5-dimethylpiperazin-1-yl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-olYield 23.1%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A mixture of the product of part (i) (2.7 g, 11 mmole) and 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl) oxirane (2.7 g, 10 mmole) in n-pentanol (30 ml) was heated under reflux for 48 hours. The solvent was then removed under reduced pressure and the residue suspended in hot ethyl acetate. After cooling, the insoluble material was removed by filtration to yield diastereomer I of the title compound (1.1 g, 22%), m.p. 212°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customThe solvent was then removed under reduced pressure
  4. temperatureAfter cooling
  5. customthe insoluble material was removed by filtration

Sources & evidence

ORD record
ord-bb7d4381a4534f7d82255682c12012b9
Source dataset
uspto-grants-1989_12
Patent number
US04885294

Reaction notes

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