Piperazine → HCID 20463845, compound

HRID 325610Notes

Reaction equation

HRID 325610 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>CCCCO>[ClH:1].[ClH:1].[I:8][C:7]1[C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 27357432-Chloro-3-iodopyridine

Product 1

HCID 20463845HCID 20463845, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-chloro-3-iodopyridine (2.39 g, 10 mmol) and piperazine (8.61 g, 100 mmol) in n-BuOH, 100 mL, was stirred at reflux under N2 for 18 h. After removing most of the n-BuOH under reduced pressure, the residue was partitioned between toluene and 10% NaOH. The toluene layer was washed further with water, dried (Na2SO4), filtered and concentrated to an oil. The pyridinylpiperazine was purified by recrystallization of the dihydrochloride salt from methanol-ethanol-ethylacetate, m.p. 185°-189° C. (dec.).

Workup

  1. temperatureat reflux under N2 for 18 h
  2. customAfter removing most of the n-BuOH under reduced pressure
  3. customthe residue was partitioned between toluene and 10% NaOH
  4. washThe toluene layer was washed further with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe pyridinylpiperazine was purified by recrystallization of the dihydrochloride salt from methanol-ethanol-ethylacetate, m.p. 185°-189° C. (dec.)

Sources & evidence

ORD record
ord-00935eeeacfe4bd7ae4b13aaeafd3b75
Source dataset
uspto-grants-1984_04
Patent number
US04442103

Reaction notes

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