Piperazine → 2-[2-(2-Chlorophenoxy)ethoxy]-3-(1-piperazinyl)quinoxaline

HRID 1789694Notes

Reaction equation

HRID 1789694 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:17]([O:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1>>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][O:18][C:17]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:16]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 220363492-Chloro-3-[2-(2-chlorophenoxy)ethoxy]quinoxaline

Product 1

HCID 220363472-[2-(2-Chlorophenoxy)ethoxy]-3-(1-piperazinyl)quinoxalineYield 22%

Procedure

Piperazine (0.580 g, 6.65 mmol) was added to the crude material from Step 1 and the resulting mixture was stirred at room temperature for 5 h. The solvent was evaporated, and the crude mixture was dissolved in DMSO and precipitated with water. The precipitate was purified by chromatography on silica gel using EtOAc/HOAc/MeOH/H2O (40:3:3:2) as eluent to afford 0.100 g (22%) of the title compound as a yellow oil. HRMS m/z calcd for C20H21CIN4O2(M)+384.1353, found 384.1334.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was dissolved in DMSO
  3. customprecipitated with water
  4. customThe precipitate was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-782c4e42a4d04b6787f69603abe08fa3
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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