4-(Cyclohexylmethyl)-2-methyl-5-{2-[4-(3-nitrophenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one → 5-{2-[4-(3-aminophenyl)piperazino]ethyl}-4-(cyclohexyl methyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514167Notes

Reaction equation

HRID 1514167 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=4)[CH2:17][CH2:16]3)=[N:11][N:10]([CH3:30])[C:9]2=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.CC#N.[Pd]>[NH2:27][C:23]1[CH:22]=[C:21]([N:18]2[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][C:12]3[N:8]([CH2:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[C:9](=[O:31])[N:10]([CH3:30])[N:11]=3)[CH2:20][CH2:19]2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 1

HCID 595364674-(Cyclohexylmethyl)-2-methyl-5-{2-[4-(3-nitrophenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 595364685-{2-[4-(3-aminophenyl)piperazino]ethyl}-4-(cyclohexyl methyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A slurry of 4-(cyclohexylmethyl)-2-methyl-5-{2-[4-(3-nitrophenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (D15; 490 mg, 1.143 mmol) and 10% Pd/C (250 mg) in MeOH (30 mL) was hydrogenated in an autoclave at 30 bar and room temperature for 4 hrs. The reaction mixture was filtered over a pad of Celite and the solvent was removed in vacuo to afford a light-brown film. This was re-dissolved in MeCN (20 mL) and filtered again through a Celite plug. The solvent was evaporated in vacuo to afford 450 mg (99%) of the title compound as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite
  2. customthe solvent was removed in vacuo
  3. customto afford a light-brown film
  4. filtrationfiltered again through a Celite plug
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5832adbcf1074fddbaa679271c093dec
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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