2-Chloro-5-methyl-pyridine → HCID 66628585, compound

HRID 1961685Notes

Reaction equation

HRID 1961685 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[CH3:9][C@@H:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1>CCO>[CH3:9][C@H:10]1[NH:11][CH2:12][CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 5813932-Chloro-5-methyl-pyridineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 66628585HCID 66628585, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-5-methyl-pyridine (127 mg, 1 mmoles), (2R)-2-methyl-piperazine (200 mg, 2 mmoles) in EtOH (3 mL) was heated in microwave to 180° C. for 5 minutes. The mixture was cooled, concentrated under reduced pressure and partitioned with DCM and the saturated aqueous sodium bicarbonate layer. The aqueous solution was extracted three times with additional DCM. The combined organic extracts were washed twice with water, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide the crude title compound.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned with DCM
  4. extractionThe aqueous solution was extracted three times with additional DCM
  5. washThe combined organic extracts were washed twice with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b53e856bfeec435294f61df1a2d80035
Source dataset
uspto-grants-2013_04
Patent number
US08415354B2

Reaction notes

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