2,5-Dichloronitrobenzene → HCID 67321994, compound

HRID 1846666Notes

Reaction equation

HRID 1846666 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][C:15](=[O:23])[CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[CH3:13]>O>[CH2:12]([O:14][C:15](=[O:23])[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:19][CH2:18]1)[CH3:13]

Participants

4

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 67321994HCID 67321994, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.500 g (2.60 mmol) of 2,5-dichloronitrobenzene and 1.0 mL (mmol) of 2-(piperdin-4-yl)-acetic acid ethyl ester is heated overnight at 105° C. The mixture is cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.803 g (94.4%) of [1-(4-chloro-2-nitro-phenyl)-piperidin-4-yl]-acetic acid ethyl ester as a red oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-ab8f857c5a3142649c6afac041b9064e
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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