Hydrochloric Acid → 5-{2-[4-(2-Methoxyphenyl)piperazino]ethyl}-4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514168Notes

Reaction equation

HRID 1514168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([NH:19][NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])=O)[CH2:11][CH2:10]1.Cl>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21](=[O:22])[NH:20][N:19]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595364632-{3-[4-(2-Methoxyphenyl)piperazino]propanoyl}-N-phenyl-1-hydrazinecarboxamide

Product 1

HCID 251843115-{2-[4-(2-Methoxyphenyl)piperazino]ethyl}-4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A suspension of 2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-N-phenyl-1-hydrazine carboxamide D5 (1.00 g, 2.50 mmol) in 2M NaOH aqueous solution (10 mL) was heated at reflux for 5 hrs. The pH of the solution was adjusted to 8 by the sequential addition of HCl 28% and NaOH, and the resulting white precipitate was filtered, washed with water and diethyl ether to afford 0.80 g (84%) 5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one E2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hrs
  3. filtrationthe resulting white precipitate was filtered
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-9c13009347e143e485bcb0d0e7941480
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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