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

HRID 565603Notes

Reaction equation

HRID 565603 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), as described above in Example 2, Step B, 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. temperaturewas heated
  2. temperatureunder reflux
  3. customThe white solid precipitated
  4. filtrationwas filtered
  5. washwashed with chloroform

Sources & evidence

ORD record
ord-f737e724aa864c3fbe88e766adc1a39b
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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