Potassium Iodide → 2,4-dihydro-2-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-methyl-4-propyl-3H-1,2,4-triazol-3-one

HRID 2106762Notes

Reaction equation

HRID 2106762 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27](=[O:28])[N:26]([CH2:29][CH2:30][CH3:31])[C:25]([CH3:32])=[N:24]2)=[CH:19][CH:18]=1.[I-].[K+].C1(O)CCCCC1.C(=O)([O-])O.[Na+]>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]2[CH2:13][CH2:14][N:16]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[C:27](=[O:28])[N:26]([CH2:29][CH2:30][CH3:31])[C:25]([CH3:32])=[N:24]4)=[CH:21][CH:22]=3)[CH2:2][CH2:3]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7966CyclohexanolHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamineHCID 516892Sodium BicarbonateHCID 151254772-(4-aminophenyl)-2,4-dihydro-5-methyl-4-propyl-3H-1,2,4-triazol-3-one

Product 1

HCID 151254782,4-dihydro-2-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-methyl-4-propyl-3H-1,2,4-triazol-3-oneYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 parts of N,N-bis(2-chloroethyl)-4-methoxybenzenamine, 23.2 parts of 2-(4-aminophenyl)-2,4-dihydro-5-methyl-4-propyl-3H-1,2,4-triazol-3-one, 2 parts of potassium iodide and 200 parts of cyclohexanol was stirred and refluxed for 5 hours using a water-separator. The reaction mixture was cooled and neutralized with a sodium hydrogen carbonate solution. The product was filtered off and dissolved in trichloromethane. The solution was filtered over silica gel and the solvent was evaporated. The residue was crystallized from 1-butanol, yielding 18 parts (44%) of 2,4-dihydro-2-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-methyl-4-propyl-3H-1,2,4-triazol-3-one; mp. 202.2° C. (int. 22).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was filtered off
  4. dissolutiondissolved in trichloromethane
  5. filtrationThe solution was filtered over silica gel
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from 1-butanol

Sources & evidence

ORD record
ord-78d1efba909f42949bb2bf0793bd8dec
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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