Potassium Carbonate → Methyl 1-(3-chloro-2-pyridinyl)4-hydroxy-4-piperidinecarboxylate

HRID 1246718Notes

Reaction equation

HRID 1246718 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:25]1[C:20]([N:8]2[CH2:9][CH2:10][C:11]([OH:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]2)=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 12343427Methyl 1-benzyl-4-hydroxypiperidine-4-carboxylate

Product 1

HCID 21904736Methyl 1-(3-chloro-2-pyridinyl)4-hydroxy-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 1-benzyl-4-hydroxy-4-piperidinecarboxylate (15.0 g, 77 mmol), 2,3-dichloropyridine (12.0 g, 81 mmol), and potassium carbonate (15.0 g, 108.7 mmol) were combined in DMF (200 mL) and heated at 90° C. for 2 days. The mixture was allowed to cool to room temperature, concentrated, and standard work-up provided a residue that was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6) to provide the title compound MS (EI, M+H)+271.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. customstandard work-up provided a residue that
  4. customwas purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6)

Sources & evidence

ORD record
ord-4fba1ae63fe14ddaaeb3c58a3a023165
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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