Water → 4-[3-(1-Benzylpiperidin-4-yl)propenoyl]nitrobenzene

HRID 976139Notes

Reaction equation

HRID 976139 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[CH:21][C:9]([C:10]([CH2:12]P(=O)(OCC)OCC)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH:23]([CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)=O.O>O1CCCC1>[CH2:31]([N:28]1[CH2:29][CH2:30][CH:25]([CH:23]=[CH:12][C:10]([C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:22][CH:21]=2)=[O:11])[CH2:26][CH2:27]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 11808775Diethyl [2-(4-nitrophenyl)-2-oxoethyl]phosphonate

Product 1

HCID 570097054-[3-(1-Benzylpiperidin-4-yl)propenoyl]nitrobenzeneYield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, 0.40 g of 64% sodium hydride was added to 3.03 g of diethyl (4-nitrobenzoylmethyl)phosphonate dissolved in 30 ml of tetrahydrofuran. After about 10 minutes, 4.07 g of 4-formyl-1-benzylpiperidine was added to the mixture. The mixture was stirred under ice cooling for 30 minutes and then stirred at room temperature for about 16 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 1.99 g of the title compound as pale yellow crystal.

Workup

  1. stirringstirred at room temperature for about 16 hours
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cdb701cf1512468aa09eb13936e1f2f9
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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