Water ethanol → HCID 70610074, compound

HRID 372455Notes

Reaction equation

HRID 372455 reaction equation
F.[NH2:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=[O:10].[H][H].[CH2:20]([OH:22])[CH3:21].O>[Pd]>[C:20]([OH:10])(=[O:22])[CH3:21].[N:12]1([C:5]2[CH:4]=[C:3]3[C:8](=[CH:7][CH:6]=2)[N:9]=[CH:21][CH:20]=[N:2]3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 19096565Water ethanolHCID 20327583HCID 20327583, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 70610074HCID 70610074, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-(3-Amino-4-nitrophenyl)piperazine hydrofluoride (2.2 g., 0.0091 mol) is hydrogenated in 100 ml. of a 1:1 ethanol-water mixture in the presence of 1.1 g. of 10% Pd on carbon at an initial pressure of 35-40 psiq of hydrogen at ambient temperature. After three equivalents of hydrogen have been absorbed, the mixture is vented to nitrogen and filtered through diatomaceous earth into a flask containing 2 ml. of 40% (by weight) aqueous glyoxal. The total filtrate is concentrated under vacuum, the aqueous solution is basified with sodium hydroxide, and then extracted with chloroform. The chloroform extract is washed with water, dried over sodium sulfate and concentrated under vacuum to an oil which is treated with 50 ml. of ethanol and 2 ml. of 10N anhydrous ethanolic-hydrogen chloride. The precipitated hydrochloride is partitioned between aqueous sodium carbonate and methylenechloride and the methylene chloride extract is washed with water, dried over sodium sulfate and concentrated to an oil which is treated with 0.5 ml. of acetic acid in 40 ml. of isopropanol and 40 ml. of ether. The crystallized 6-(1-piperazinyl)quinoxaline acetate, m.p. 147°-148.5° C. is collected by filtration.

Workup

  1. customat ambient temperature
  2. filtrationfiltered through diatomaceous earth into a flask
  3. additioncontaining 2 ml
  4. concentrationThe total filtrate is concentrated under vacuum
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washis washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum to an oil which
  10. additionis treated with 50 ml
  11. customThe precipitated hydrochloride is partitioned between aqueous sodium carbonate and methylenechloride
  12. extractionthe methylene chloride extract
  13. washis washed with water
  14. dry with materialdried over sodium sulfate
  15. concentrationconcentrated to an oil which
  16. additionis treated with 0.5 ml
  17. filtrationThe crystallized 6-(1-piperazinyl)quinoxaline acetate, m.p. 147°-148.5° C. is collected by filtration

Sources & evidence

ORD record
ord-3069081e0d714287a90a41d915f4b930
Source dataset
uspto-grants-1978_05
Patent number
US04091101

Reaction notes

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