Piperazine → HCID 15592130, compound

HRID 2417610Notes

Reaction equation

HRID 2417610 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CO[C:9]1[C:10](=[O:16])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1>CO>[N:1]1([C:11]2[C:10](=[O:16])[CH:9]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][N:4]([C:9]2[C:10](=[O:16])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 165462-Methoxy-2,4,6-cycloheptatrien-1-one

Product 1

HCID 15592130HCID 15592130, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
95 °C

Procedure

To a solution of piperazine (7.74 g) in methanol (10 ml) at 70° C., a solution of 2-methoxy-2,4,6-cycloheptatrien-1-one (8.16 g) in methanol (50 ml) was added drop by drop. The reaction mixture was heated at 95° C. for 5 hr, cooled and evaporated. The residue was dissolved in chloroform and water. The organic extract was separated, dried and evaporated. The residue was chromatographed on silica gel (250 g) using chloroform then 5% methanol in chloroform, increasing gradually the concentration of methanol up to 20%. The product was recrystallized from methanol to yield 2.9 g of the title compound: mp 184°-186° C.; ir(CHCl3) 1565 cm-1 ; uv max(MeOH) 355 (ε=19075), 256 (ε=29080) and 223 nm (ε=22460); nmr(CDCl3) δ3.55 (m, 8H) and 7.0 (m, 10H); and Anal. Calcd for C 18 H18N2O2 : C, 73.45% H, 6.16% N, 9.52% and Found: C, 73.76% H, 6.17% N, 9.45%.

Workup

  1. temperaturecooled
  2. customevaporated
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionThe organic extract
  5. customwas separated
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (250 g)
  9. temperature5% methanol in chloroform, increasing gradually the concentration of methanol up to 20%
  10. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-364491d2b57f4497b900a6a7292ba9d7
Source dataset
uspto-grants-1984_09
Patent number
US04469694

Reaction notes

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