Hydrochloric Acid → 1-(4-Nitrophenyl)piperidine-4-carboxylic acid

HRID 2174692Notes

Reaction equation

HRID 2174692 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>C(O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 2796870ethyl 1-(4-nitrophenyl)piperidine-4-carboxylate

Product 1

HCID 27672651-(4-Nitrophenyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 1-(4-nitrophenyl)piperidine-4-carboxylic acid ethyl ester (2.78 g, 10 mmol) obtained in Example 2(1) was dissolved in ethanol (10 ml), and a 4 N sodium hydroxide aqueous solution (5 ml, 20 mmol) was added thereto. The mixture was refluxed under heat for 1 hour. After cooling to room temperature, water (30 ml) and 2 N hydrochloric acid (10 ml) were added to the mixture, and the precipitate was collected by filtration, thereby obtaining 1-(4-nitrophenyl)piperidine-4-carboxylic acid (2.47 g, 97%) as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heat for 1 hour
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8c32e617867840e598c1b1e615572752
Source dataset
uspto-grants-2015_06
Patent number
US09062035B2

Reaction notes

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