Diphenyl Ether → 4-Benzyl-1-(3-chloro-2-pyrazinyl)-cis-2,6-dimethylpiperazine

HRID 493330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493330
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([N:16]1[CH2:21][C@H:20]([CH3:22])[NH:19][C@H:18]([CH3:23])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CCCC)CCCC)CCC.C1(OC2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:9]([N:16]1[CH2:17][C@@H:18]([CH3:23])[N:19]([C:2]2[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=2)[C@@H:20]([CH3:22])[CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 7583Diphenyl EtherHCID 7622TributylamineHCID 785752,3-DichloropyrazineHCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazine

Produkt 1

HCID 536601384-Benzyl-1-(3-chloro-2-pyrazinyl)-cis-2,6-dimethylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

A mixture of 2,3-dichloropyrazine (4.9 g, 32.9 mmol), 1-benzyl-cis-3,5-dimethylpiperazine (5.9 g, 29.0 mmol), tributylamine (5.9 g, 32 mmol) and diphenyl ether (70 mL) was heated in a sealed tube at 220° C. for 3 days. The reaction mixture was cooled to ambient temperature and EtOAc (200 mL) and toluene (100 mL) were added. The organic phase was extracted with 5 M aqueous HCl (×3) and the combined aqueous phases were extracted with CHCl3 (×3). The combined organic layers, which contained the product, were washed with aqueous NaOH (5 M), dried (MgSO4), and the solvent was evaporated. The crude product (0.96 g), about 80% pure based on GC, was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe organic phase was extracted with 5 M aqueous HCl (×3)
  3. extractionthe combined aqueous phases were extracted with CHCl3 (×3)
  4. washwere washed with aqueous NaOH (5 M)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-70452dfa31b140209022565b4cb90eb8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

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