Potassium Carbonate → HCID 61375242, compound

HRID 2424422Notes

Reaction equation

HRID 2424422 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:13]2[CH2:14][CH2:15][CH:10]([OH:9])[CH2:11][CH2:12]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 6933243-Bromo-2-chloropyridine

Product 1

HCID 61375242HCID 61375242, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-2-chloropyridine (5.95 g, 30.92 mmol), 4-hydroxypiperidine (5 g, 49.43 mmol) and potassium carbonate (15.03 g, 108.75 mmol) were combined in DMF (200 ml) and heated to 120° C. overnight. The solvent was removed and the residues partitioned between EtOAc and water. The aqueous layer was re-extracted with EtOAc and the combined organics washed with water, dried and concentrated. The crude product was purified by column chromatography. Elution with 20-75% EtOAc/pet. ether yielded the product as a yellow oil (5.1 g). δH (CDCl3, 400 MHz): 1.60-1.61 (1H, m), 1.68-1.79 (2H, m), 2.01-2.07 (2H, m), 2.98-3.04 (2H, m), 3.64-3.69 (2H, m), 3.86-3.91 (1H, m), 6.74-6.77 (1H, m), 7.77-7.79 (1H, dd), 8.21-8.22 (1H, m).

Workup

  1. customThe solvent was removed
  2. customthe residues partitioned between EtOAc and water
  3. extractionThe aqueous layer was re-extracted with EtOAc
  4. washthe combined organics washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washElution with 20-75% EtOAc/pet. ether

Sources & evidence

ORD record
ord-43a65959a296420b9a1a249f02553555
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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