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

HRID 16699

Reaction equation

HRID 16699 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), and thereto is added ethyl isonicotinate (10.00 g). The reaction solution is then 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, and 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-cc361223dfd14718a49e0b82a2f7cfe8
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Linked notes

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