Hydrochloric Acid → 4-(Cyclohexylmethyl)-5-{2-[4-(3-nitrophenyl)piperazin-1-yl]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514160Notes

Reaction equation

HRID 1514160 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[CH2:18][CH2:17]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>[OH-].[Na+]>[CH:1]1([CH2:7][N:8]2[C:13]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=4)[CH2:18][CH2:17]3)=[N:12][NH:11][C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59536466N-(Cyclohexylmethyl)-2-{3-[4-(3-nitrophenyl)piperazin-1-yl]propanoyl}hydrazine carboxamide

Product 1

HCID 595364714-(Cyclohexylmethyl)-5-{2-[4-(3-nitrophenyl)piperazin-1-yl]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of N-(cyclohexylmethyl)-2-{3-[4-(3-nitrophenyl)piperazin-1-yl]propanoyl}hydrazine carboxamide D8 (0.70 g, 1.62 mmol) in 2M NaOH aqueous solution (10 mL) was heated at reflux for 5 hrs, then cooled to room temperature and brought to pH 8 by the drop-wise addition of HCl 28%. The resulting precipitate was filtered, washed with water and diethyl ether to afford 0.60 g (89%) 4-(cyclohexylmethyl)-5-{2-[4-(3-nitrophenyl)piperazin-1-yl]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D9 as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-5868ea1694ed429b884610555172589f
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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