1-Benzoyl-4-methyl-4-piperidinecarboxylic acid → 4-Methylpiperidine-4-carboxylic acid

HRID 1770098Notes

Reaction equation

HRID 1770098 reaction equation
C([N:9]1[CH2:17][CH2:16][C:12]([CH3:18])([C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1>Cl>[CH3:18][C:12]1([C:13]([OH:15])=[O:14])[CH2:16][CH2:17][NH:9][CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 200954061-Benzoyl-4-methyl-4-piperidinecarboxylic acid

Product 1

HCID 221045794-Methylpiperidine-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-Benzoyl-4-methyl isonipecotic acid (1.21 g, 4.88 mmol) was dissolved in 20 mL of 6N HCl and refluxed overnight. The mixture was cooled and benzoic acid removed by filtration. The filtrate was evaporated and crystallization from acetone/dichloromethane provided 0.62 g of 4-methyl isonipecotic acid (90%). 1H NMR (300 MHz DMSO d6) δ9.0 (s, 1H), 3.1 (m, 2H), 2.7 (m, 2H), 2.0 (m, 2 H), 1.6 (m, 2H), 1.1 (s, 3H).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled
  3. custombenzoic acid removed by filtration
  4. customThe filtrate was evaporated
  5. customcrystallization from acetone/dichloromethane

Sources & evidence

ORD record
ord-71123c1c499f4ce384ceb33b186987e6
Source dataset
uspto-grants-1995_01
Patent number
US05385908

Reaction notes

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