Sodium Chloride → 4-Nitro-N-[2-(4-benzoyl-1-piperidinyl)ethyl]-N-(3-pyridyl)benzamide

HRID 2517

Reaction equation

HRID 2517 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1.[I-].[Na+].[Cl-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([N:10]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([C:30](=[O:37])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:28][CH2:29]2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 83332Pyridine, 3-(p-nitrobenzamido)-HCID 10824664(1-(2-Chloroethyl)piperidin-4-yl)(phenyl)methanone

Product 1

HCID 196900494-Nitro-N-[2-(4-benzoyl-1-piperidinyl)ethyl]-N-(3-pyridyl)benzamideYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

In an atmosphere of argon, 4-nitro-N-(3-pyridyl)benzamide (973 mg, 4.00 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (176 mg, 60%, 4.40 mmol) at room temperature, stirred for 1 hour at 60° C., and added dropwise 1-(2-chloroethyl)-4-benzoylpiperidine (1.38 g, 5.49 mmol) and a catalytically effective amount of a DMF solution (12 ml) of sodium iodide. After 4 hours of stirring at 60° C., the reaction solution was mixed with saturated sodium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by recrystallization (ethyl acetate-ether) to obtain 439.6 mg (24.0%) of the title compound in a light yellow powder form.

Workup

  1. customat room temperature
  2. stirringAfter 4 hours of stirring at 60° C.
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThereafter, the solvent was removed by evaporation
  7. customthe resulting residue was purified by recrystallization (ethyl acetate-ether)

Sources & evidence

ORD record
ord-210fb1b1e78248f89d667958215bdb36
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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