Water → 1-(3-Dimethylcarbamoyl-4-nitrophenyl)piperidine-4-carboxylic acid ethyl ester

HRID 423281Notes

Reaction equation

HRID 423281 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].[CH2:16]([O:18][C:19]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:16]([O:18][C:19]([CH:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])[CH:12]=2)[CH2:23][CH2:22]1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamide

Product 1

HCID 666765811-(3-Dimethylcarbamoyl-4-nitrophenyl)piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-N,N-dimethyl-2-nitrobenzamide (1.131 g), 4-piperidinecarboxylic acid ethyl ester (0.77 mL), and potassium carbonate (1.4 g) were reacted in N,N′-dimethylformamide (20 mL) at 100° C. for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and concentrated to give the title compound (1.578 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-363b65ca349f48d0afdee48993ed47b5
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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