Piperazine → HCID 5255691, compound

HRID 1421248Notes

Reaction equation

HRID 1421248 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 mL 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 (3×). 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 CH2Cl2) 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 (3×)
  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 CH2Cl2)

Sources & evidence

ORD record
ord-6542efc1c17f47e99e6cd354a2ff0759
Source dataset
uspto-grants-2000_06
Patent number
US06075025

Reaction notes

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