1-Methylpiperazine → 1,2-Dihydro-8-(4-methylpiperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

HRID 2309688Notes

Reaction equation

HRID 2309688 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([N+:6]([O-:21])=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]3[N:9]2[CH2:12][CH2:13][N:14]=3)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(O)(C)C>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:11]=[C:10]3[C:5]([N+:6]([O-:21])=[C:7]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:8]4[N:9]3[CH2:12][CH2:13][N:14]=4)=[CH:4][CH:3]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 139586071,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

Product 1

HCID 139586081,2-Dihydro-8-(4-methylpiperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxideYield 17.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide (3.5 g, 0.012 mol) and N-methylpiperazine (15 ml, 0.13 mol) were heated at 100° C. in isopropanol (5 ml) for 16 hrs. The solvent was removed in vacuo and the residue was dissolved in dichloromethane. The resulting solution was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulphate and concentrated in vacuo to yield a dark oil which was chromatographed on silica gel in 2% methanol/chloroform to yield a red solid. The red solid was recrystallized from ethyl acetate to yield 1,2-dihydro-8-(4-methylpiperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide, (0.75 g), as deep red crystals m.p. 179°-183° C., (δ(CDCl3) 2.38 (3H,s) 2.58 (4H,m) 3.37 (4H,m) 3.95-4.24 (4H,m) 6.08 (1H,d,J=3.5Hz), 6.62 (1H,dd,J=9 and 3.5Hz), 7.38-7.5 (3H,m), 7.84 (2H,m), and 8.11 (1H,d,J=9 Hz)), represented by the structural formula: ##STR17##

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto yield a dark oil which
  7. customwas chromatographed on silica gel in 2% methanol/chloroform
  8. customto yield a red solid
  9. customThe red solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5e3c5e28eae0487dba151cfb389db6dd
Source dataset
uspto-grants-1987_09
Patent number
US04696928

Reaction notes

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