Piperazine → HCID 23194053, compound

HRID 263916Notes

Reaction equation

HRID 263916 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH:8]1[C:20]2[NH:19][C:18](=[O:21])[C:17](=[O:22])[NH:16][C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2>O1CCCC1>[N:1]1([CH:8]2[C:20]3[NH:19][C:18](=[O:21])[C:17](=[O:22])[NH:16][C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837Piperazine2×HCID 19035982HCID 19035982, compound

Product 1

HCID 23194053HCID 23194053, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperazine (1.1 g, 12.8 mmol) was suspended in 15 ml of dry tetrahydrofuran at -20° C. 9-Chloro-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione (1.5 g, 6.4 mmol) was added over 25 min. and the temperature was slowly rised to room temperature while stirring. After 20 hours another portion of piperazine (0.55 g, 6.4 mmol) was added and stirring was continued for 72 hours. The reaction mixture was evaporated in vacuo to dryness and the remanence was suspended in 10 ml 6M HCl. The product was filtered off and washed with 1M HCl and dried to give 1.7 g of the crude product, which was purified by dissolving in aqueous sodium hydroxide and precipitated by adding to hydrochloric acid. The procedure was repeated and the product was finally washed with ethanol and dried to give 0.64 g (27%) of the title compound as a hydrochloride. M.p. 259°-263° C. 1H-NMR (DMSO-d6, δ): 2.65-3.15 (m, 8H), 4.7 (s, 1H), 7.17 (t, 1H), 7.34 (t, 1H), 7.45 (d, 1H), 7.57 (d, 1H), 8.93 (s, 2H), 11.8 (s, 1H), 12.3 (s, 1H).

Workup

  1. customwas slowly rised to room temperature
  2. stirringstirring
  3. customThe reaction mixture was evaporated in vacuo to dryness
  4. filtrationThe product was filtered off
  5. washwashed with 1M HCl
  6. customdried
  7. customto give 1.7 g of the crude product, which
  8. customwas purified
  9. dissolutionby dissolving in aqueous sodium hydroxide
  10. customprecipitated
  11. additionby adding to hydrochloric acid
  12. washthe product was finally washed with ethanol
  13. customdried

Sources & evidence

ORD record
ord-c94fcf6515fd4f18b30147b9407502c5
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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