Piperazine → 2-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)Pyrazine

HRID 2182136

Reaktionsgleichung

Reaktionsgleichung von HRID 2182136
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[CH:5]=[N:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(O)C>[N:18]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[C:13]#[N:14])[N:7]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 224819733-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrile

Produkt 1

HCID 98573352-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)Pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(6-chloro-pyrazin-2-yloxymethyl)-benzonitrile I-3a (3.53 g, 14.4 mmol) and piperazine (12.4 g, 143.70 mmol) in ethanol (144 mL) was stirred under reflux for 48 h. The reaction mixture was concentrated to dryness and the residue was dissolved in ethyl acetate (300 mL). The ethyl acetate solution was washed with H2O (4×125 mL), brine (125 mL), dried (Na2SO4), filtered, and concentrated to dryness. The crude material was chromatographed over Silica Gel (40 g) using 5% methanol/methylene chloride with 1% NH4OH as the eluant to give 3.03 g of the desired product (I-3b) as a white solid.

Aufarbeitung

  1. temperatureunder reflux for 48 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
  4. washThe ethyl acetate solution was washed with H2O (4×125 mL), brine (125 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material was chromatographed over Silica Gel (40 g)

Quellen und Nachweise

ORD-Eintrag
ord-afc22ffcb6c54661ba92ff115196f07b
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894050B2

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