Potassium Hydroxide → 4-(m-Toluidino)-1-benzylpiperidine-4-carboxylic acid

HRID 443299Notes

Reaction equation

HRID 443299 reaction equation
[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:12](N)=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[K+]>C(O)CO.O.C(O)(=O)C>[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:12]([OH:25])=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 211931981-Benzyl-4-(3-methylphenylamino)isonipecotamide

Product 1

HCID 211934454-(m-Toluidino)-1-benzylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1-benzyl-4-(3-methylphenylamino)-isonipecotamide (4.5 g, 13.9 mmol) and potassium hydroxide (3.g, 53.5 mmol) in ethylene glycol (35 mL) was heated under reflux. The resulting mixture was diluted with water and neutralized with acetic acid. The white solid precipitated was filtered, washed with chloroform to provide 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylic acid.

Workup

  1. temperatureunder reflux
  2. customThe white solid precipitated
  3. filtrationwas filtered
  4. washwashed with chloroform

Sources & evidence

ORD record
ord-7c1864e1d3a84e0fb738ef33ea8fc92a
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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