Ethanol → HCID 68523798, compound

HRID 1932460Notes

Reaction equation

HRID 1932460 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

3-(4-hydroxyphenyl)-1-(4-piperonylpiperazin-1-yl)propan-1-one (0.38 g, 1.0 mmol) was dissolved in DMF (6 mL). To the resulting solution was added 60% sodium hydride (0.05 g, 1.2 mmol) and 2-chloro-4-methyl-5-nitropyridine (0.196 g, 1.1 mmol), and the resulting reaction solution was stirred overnight at room temperature. To the reaction solution was added saturated aqueous ammonium chloride, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate), to thereby yield the intermediate product 3-(4-(4-methyl-5-nitropyridin-2-yloxy)phenyl)-1-(4-piperonylpiperazin-1-yl)propan-1-one. 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-209064a8d75e4c9bb220f457605c75a9
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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