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

HRID 991623Notes

Reaction equation

HRID 991623 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 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
  4. customThe precipitate was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-10b4add3178b4f6194e41c961f0bf20a
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

Loading…