Triethylamine → 1-(Pyridin-4-yl)piperidine-4-carboxylic acid

HRID 491831Notes

Reaction equation

HRID 491831 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:16]([O:24]CC)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>C(O)C.O>[N:6]1[CH:7]=[CH:8][C:3]([N:20]2[CH2:21][CH2:22][CH:17]([C:16]([OH:24])=[O:23])[CH2:18][CH2:19]2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15291Ethyl isonicotinateHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidYield 78.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloropyridine hydrochloride (9.55 g) and triethylamine (26.0 ml) are dissolved in ethanol (10 ml) and water (30 ml), thereto is added ethyl isonicotinate (10.00 g), and then the reaction solution is heated at 150° C. for 96 hours in a sealed tube. After allowing to cool, ethanol is added to the reaction solution and the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, the resulting residue is suspended in chloroform, the precipitates are collected by filtration and recrystallized from water-N,N-dimethylformamide to give the title compound (10.34 g).

Workup

  1. temperatureto cool
  2. customthe insoluble materials are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. filtrationthe precipitates are collected by filtration
  5. customrecrystallized from water-N,N-dimethylformamide

Sources & evidence

ORD record
ord-9eed781032ea4cb2a3660770913f9d40
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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