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

HRID 1514169Notes

Reaction equation

HRID 1514169 reaction equation
[CH:1]1([NH:9][C:10]([NH:12][NH:13][C:14](=O)[CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>[OH-].[Na+]>[CH:1]1([N:9]2[C:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])[CH2:19][CH2:18]3)=[N:13][NH:12][C:10]2=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59536460N-Cyclooctyl-2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-1-hydrazinecarboxamide

Product 1

HCID 251843794-cyclooctyl-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 47%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of N-cyclooctyl-2-{3-[4-(2-methoxyphenyl)piperazino]propanoyl}-1-hydrazinecarboxamide D3 (0.40 g, 0.93 mmol) in 2M NaOH aqueous solution (10 mL) was heated at reflux for 18 hrs. The solution was cooled to room temperature and the pH was adjusted to 8 by the drop-wise addition of HCl 28%. The resulting precipitate was filtered to afford a white solid, which was twice boiled with ethyl acetate and filtered while hot. The filtrates were combined and evaporated under reduced pressure to afford 0.18 g (47%) 4-cyclooctyl-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one E10.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hrs
  3. filtrationThe resulting precipitate was filtered
  4. customto afford a white solid, which
  5. filtrationfiltered while hot
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ba03db0d0e2489fa11fbeb21cfdb191
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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