Piperazine → HCID 5255691, compound

HRID 863432Notes

Reaction equation

HRID 863432 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15](Cl)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.CCN(CC)CC.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 10778001HCID 10778001, compound

Product 1

HCID 5255691HCID 5255691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 10.0 g (37.9 mmol) of 8,11-dichloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine and 1.0 m/of Et3N in 200 mL of dry THF at room temperature and under a nitrogen atmosphere was added 33.0 g of piperazine. The mixture was stirred at room temperature for 22.5 hours and then refluxed for 5.5 hours. It was then cooled to room temperature, poured into 250 mL of 5% aqueous NaOH, and extracted with CH2Cl2 (3X). The combined organic portions were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (2→5% MeOH saturated with NH4OH in CH2 Cl2) to yield the title compound as a glass.

Workup

  1. temperaturerefluxed for 5.5 hours
  2. temperatureIt was then cooled to room temperature
  3. extractionextracted with CH2Cl2 (3X)
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (2→5% MeOH saturated with NH4OH in CH2 Cl2)

Sources & evidence

ORD record
ord-40ac736076be4ea0a6d6c6b0ceab64d8
Source dataset
uspto-grants-1998_02
Patent number
US05721236

Reaction notes

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