Sodium hydride → HCID 68526210, compound

HRID 884107Notes

Reaction equation

HRID 884107 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.

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-f204398be12c4f01a788229917369297
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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