N-(Cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-1-hydrazinecarboxamide → 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514170Notes

Reaction equation

HRID 1514170 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]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:18][CH2:17]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[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]=[CH:24][C:23]=4[O:28][CH3:29])[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

3

Reactant 1

HCID 59536472N-(Cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-1-hydrazinecarboxamide

Product 1

HCID 251844534-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 57.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of N-(cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-1-hydrazinecarboxamide D4 (0.40 g, 0.96 mmol) in 2M NaOH aqueous solution (10 mL) was heated at reflux for 7 hrs. The resulting precipitate was filtered, washed with water and diethyl ether to afford 0.22 g (57%) 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one E17 as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hrs
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-e4b8d81e8ab44815b19b081e43c443fe
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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