Ethanol → HCID 68523798, compound

HRID 884108Notes

Reaction equation

HRID 884108 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:37]=[CH:36][C:35]5[O:34][CH2:33][O:32][C:31]=5[CH:30]=4)[CH2:24][CH2:23]3)=[O:21])=[CH:14][CH:13]=2)[CH:3]=1.C(O)C>[C].[Pd].O1CCOCC1>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][C:20]([N:22]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]4[CH:37]=[CH:36][C:35]5[O:34][CH2:33][O:32][C:31]=5[CH:30]=4)[CH2:26][CH2:27]3)=[O:21])=[CH:16][CH:17]=2)=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 68526210HCID 68526210, compound

Product 1

HCID 68523798HCID 68523798, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The 3-(4-(4-methyl-5-nitropyridin-2-yloxy)phenyl)-1-(4-piperonylpiperazin-1-yl)propan-1-one was dissolved in a mixed solvent consisting of ethanol (4 mL) and dioxane (1 mL). To this solution was added 10% palladium-carbon (0.034 g), and the resulting solution was subjected to catalytic reduction for 8 hours at atmospheric pressure and room temperature. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (dichloromethane:methanol=20:1), to thereby yield 0.22 g of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-58fff89fd2cc469d96a4d3b12d6aa47f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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