Water → HCID 59454338, compound

HRID 1914754Notes

Reaction equation

HRID 1914754 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:9]=2[C:17](=[O:19])[CH3:18])[CH2:4][CH2:3]1.C1CCCCC=1.C1COCC1.O>Cl.[Pd].CCO>[NH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[C:9]=1[C:17](=[O:19])[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8079CyclohexeneHCID 594543161-[2-(4-Methyl-1-piperazinyl)-6-nitrophenyl]ethanone

Product 1

HCID 59454338HCID 59454338, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-[2-(4-methyl-piperazin-1-yl)-6-nitro-phenyl]-ethanone (270 mg, 1.02 mmol) in a mixture (1:1:1.5:2.5) of cyclohexene:THF:H2O:EtOH (12 ml), Pd/C 10% (328 mg) and two drops of HCl 37% were added. The mixture was heated at 70° C. for 3 hours. The Pd was filtered from the reaction and the solvents were removed from the filtrate under reduced pressure. The crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol 9:1:1), to give the final compound (225 mg, 95% yield) as orange oil. This was treated with HCl in dioxane, in order to obtain a more manageable solid.

Workup

  1. filtrationThe Pd was filtered from the reaction
  2. customthe solvents were removed from the filtrate under reduced pressure
  3. customThe crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol 9:1:1)

Sources & evidence

ORD record
ord-ae06d0dca36d475ca2fc3053e0203e62
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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