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

HRID 1514161Notes

Reaction equation

HRID 1514161 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][NH:10][C:9]2=[O:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[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:30])[NH:10][N:11]=3)[CH2:20][CH2:19]2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 1

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

Product 1

HCID 595364625-{2-[4-(3-aminophenyl)piperazin-1-yl]ethyl}-4-(cyclohexylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(cyclohexylmethyl)-5-{2-[4-(3-nitrophenyl)piperazin-1-yl]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D9 (0.30 g, 0.72 mmol) in methanol (20 mL), a catalytic amount of 10% Pd/C was added and the slurry was pressurized to 20-30 bar in an autoclave for 3 days. The catalyst was filtered through a Celite pad and the filtrate was evaporated to afford 0.26 g (93%) 5-{2-[4-(3-aminophenyl)piperazin-1-yl]ethyl}-4-(cyclohexylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one D10 as an orange semi-solid.

Workup

  1. filtrationThe catalyst was filtered through a Celite pad
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0c2a0904ec2e40049830510bf5dd213b
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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