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

HRID 493279Notes

Reaction equation

HRID 493279 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 T he 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 C20H21ClN4O2 (M)+ 384.1353, found 384.1334.

Workup

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

Sources & evidence

ORD record
ord-d1df65f2546847b5b7de479aeef17de6
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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