Piperidine → 5-Bromo-2-(piperidin-1-yl)pyridine

HRID 646165Notes

Reaction equation

HRID 646165 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[N:6][CH:7]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86593682HCID 86593682, compound

Product 1

HCID 164142095-Bromo-2-(piperidin-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of trifluoromethanesulfonic acid 5-bromopyrid-2-yl ester (see step (a) above; 1.5 g, 4.9 mmol), piperidine (1.07 mL, 10.8 mmol) and DMF (5 mL) was heated at 40° C. for 3 h. DMF was then removed in vacuo, water (20 mL) was added to the residue and the product extracted with EtOAc (3×15 mL) and CH2Cl2 (15 mL). The combined organic extracts were washed with brine and dried (Na2SO4). After removal of the solvent, the residue was dissolved in Et2O and HCl (4M in dioxane; 4 mL) was added.

Workup

  1. customDMF was then removed in vacuo, water (20 mL)
  2. additionwas added to the residue
  3. extractionthe product extracted with EtOAc (3×15 mL) and CH2Cl2 (15 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of the solvent
  7. dissolutionthe residue was dissolved in Et2O
  8. additionHCl (4M in dioxane; 4 mL) was added

Sources & evidence

ORD record
ord-5e18a207fb984b58bcb0ac15508d974d
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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