Sodium borohydride → 1-[4-(2-Amino-phenyl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone

HRID 1810964Notes

Reaction equation

HRID 1810964 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[CH2:13][CH2:12]2)=[O:10])[N:3]=1.[BH4-].[Na+]>[Pd].CO>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH2:8][N:4]2[C:5]([CH3:7])=[CH:6][C:2]([CH3:1])=[N:3]2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 270079912-(3,5-Dimethyl-pyrazol-1-yl)-1-[4-(2-nitro-phenyl)-piperazin-1-yl]-ethanone

Product 1

HCID 595487551-[4-(2-Amino-phenyl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanoneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask containing 2-(3,5-dimethyl-pyrazol-1-yl)-1-[4-(2-nitro-phenyl)-piperazin-1-yl]-ethanone (0.201 g, 0.584 mmol) and Pd/C (0.100 g) under Ar is added 10 mL of MeOH. To this mixture NaBH4 (0.022 g, 0.584 mmol) is added and the mixture is stirred for 1 h. The mixture is filtered through diatomaceous earth and concentrated to dryness. The residue is diluted with 100 mL CH2Cl2 and quenched with 50 mL of saturated NH4Cl. The organic phase is dried with MgSO4, filtered and concentrated to give 1-[4-(2-amino-phenyl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone in 93% yield.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. concentrationconcentrated to dryness
  3. additionThe residue is diluted with 100 mL CH2Cl2
  4. customquenched with 50 mL of saturated NH4Cl
  5. dry with materialThe organic phase is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eb676799527e42b1995de84835101479
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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