Sodium hydride → HCID 68526210, compound

HRID 1932459Notes

Reaction equation

HRID 1932459 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:27]=[CH:26][C:25]4[O:24][CH2:23][O:22][C:21]=4[CH:20]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:31]1[CH:36]=[C:35]([CH3:37])[C:34]([N+:38]([O-:40])=[O:39])=[CH:33][N:32]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:37][C:35]1[C:34]([N+:38]([O-:40])=[O:39])=[CH:33][N:32]=[C:31]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]4[CH:27]=[CH:26][C:25]5[O:24][CH2:23][O:22][C:21]=5[CH:20]=4)[CH2:16][CH2:17]3)=[O:11])=[CH:6][CH:7]=2)[CH:36]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 68525624HCID 68525624, compound

Product 1

HCID 68526210HCID 68526210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e3a99bd1ea4e47febec5358d5e5b4f96
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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