Piperazine → 1-(9H-Fluoren-9-yl)piperazine

HRID 36615Notes

Reaction equation

HRID 36615 reaction equation
Cl[CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(N(CC)CC)C.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C1COCC1>[CH:13]1[C:14]2[CH:2]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 23115Fluorene, 9-chloro-

Product 1

HCID 4102051-(9H-Fluoren-9-yl)piperazineYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9-chlorofluorene (8.4 g), triethylamine (0.85 mL) and piperazine (27 g) in THF (200 mL) was refluxed under argon for 6 hours. It was then filtered and the solvent was removed under vacuum. The crude product was washed with water, chromatographed on silica gel and eluted with 5% MeOH saturated with NH3 in CH2Cl2 to afford the title compound (8.5 g).

Workup

  1. filtrationIt was then filtered
  2. customthe solvent was removed under vacuum
  3. washThe crude product was washed with water
  4. customchromatographed on silica gel
  5. washeluted with 5% MeOH saturated with NH3 in CH2Cl2

Sources & evidence

ORD record
ord-b09a462be86c448d80e10e2b78d2cf19
Source dataset
uspto-grants-1995_05
Patent number
US05416087

Reaction notes

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