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

HRID 1068489Notes

Reaction equation

HRID 1068489 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-bfc38e58f55841e2893ba1676b327365
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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