Iodoacetamide → 2-[4-(1,2-Dihydro-5-oxido-4-phenylimidazo[1,2-a]-quinoxalin-8-yl)piperazinyl]acetamide

HRID 2309693Notes

Reaction equation

HRID 2309693 reaction equation
C(N(CC)CC)C.I[CH2:9][C:10]([NH2:12])=[O:11].[C:13]1([C:19]2[C:20]3[N:21]([CH2:36][CH2:37][N:38]=3)[C:22]3[C:27]([N+:28]=2[O-:29])=[CH:26][CH:25]=[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:23]=3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[O-:29][N+:28]1[C:27]2[C:22](=[CH:23][C:24]([N:30]3[CH2:35][CH2:34][N:33]([CH2:9][C:10]([NH2:12])=[O:11])[CH2:32][CH2:31]3)=[CH:25][CH:26]=2)[N:21]2[CH2:36][CH2:37][N:38]=[C:20]2[C:19]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 8471TriethylamineHCID 99501581,2-Dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide

Product 1

HCID 139586192-[4-(1,2-Dihydro-5-oxido-4-phenylimidazo[1,2-a]-quinoxalin-8-yl)piperazinyl]acetamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (0.75 g, 0.0072 mol.) was added to a solution of iodoacetamide (0.59 g, 0.0032 mol.) and 1,2-dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide (1.0 g, 0.0029 mol.) in ethanol (50 ml) and the reaction mixture stirred overnight at room temperature. The resulting precipitate was removed by filtration, washed with ethanol and then ether. Recrystallization from ethanol yielded 2-[4-(1,2-dihydro-5-oxido-4-phenylimidazo[1,2-a]-quinoxalin-8-yl)piperazinyl]acetamide, (0.63 g) as bright yellow crystals, m.p. 225°-227° C. (Found: C, 63.50; H, 5.89; N, 19.72%; C22H24N6O6.O.75H2O requires C, 63.23; H, 6.11; N, 20.12%) represented by the structural formula: ##STR32##

Workup

  1. customThe resulting precipitate was removed by filtration
  2. washwashed with ethanol
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-634ecd35dbcb45ec9f7f39ce41cd0a7e
Source dataset
uspto-grants-1987_09
Patent number
US04696928

Reaction notes

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