Hydrochloric Acid → 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514165Notes

Reaction equation

HRID 1514165 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][CH:15]([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)[CH3:16])=[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][CH:15]([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)[CH3:16])=[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 59536457N-(cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide

Product 1

HCID 251847324-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 48.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-(Cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide D13 (0.90 g, 2.08 mmol) in 2M NaOH aqueous solution (20 mL) was heated at reflux for 18 hrs. The pH was adjusted to 8 with conc. HCl and the resulting yellow slurry was extracted twice with DCM (50 mL and 20 mL). The combined organic extracts were filtered and DCM evaporated under reduced pressure to a light yellow glassy solid. Purification by flash chromatography (Silica gel 60 Å, 45 μm 10% methanol in dichloromethane) afforded 0.42 g (48.8%) 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D14 as a cream solid.

Workup

  1. temperatureat reflux for 18 hrs
  2. extractionthe resulting yellow slurry was extracted twice with DCM (50 mL and 20 mL)
  3. filtrationThe combined organic extracts were filtered
  4. customDCM evaporated under reduced pressure to a light yellow glassy solid
  5. customPurification by flash chromatography (Silica gel 60 Å, 45 μm 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ef8ed5cbfb7941729cc8a028125b1892
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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