Piperazine → 1-[6-(2-Thienylmethoxy)-2-pyridinyl]piperazine

HRID 1357586

Reaktionsgleichung

Reaktionsgleichung von HRID 1357586
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl>[S:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[CH2:9][O:8][C:4]1[N:3]=[C:2]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 181869442-Chloro-6-(2-Thienylmethoxy)Pyridine

Produkt 1

HCID 181868551-[6-(2-Thienylmethoxy)-2-pyridinyl]piperazineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of the product from step 1 above (1.35 g, 5.98 mmol), piperazine (1.55 g, 17.9 mmol) and K2CO3 (0.91 g, 6.58 mmol) in acetonitrile (5 mL) was heated at 125 125° C. for 6.5 h in a sealed pyrex flask. The reaction mixture was diluted with dichlorometane, filtered and concentrated in vacuo. The semi-solid residue was purified by silica gel (16×4 cm) chromatography using CHCl3/MeOH (9:1) as eluent. Solvents were evaporated and the oily residue was redissolved in CHCl3/ether (1:1). Filtration and concentration in vacuo furnished 0.78 g (47%) of the title compound as a beige oil. HRMS m/z calcd for C14H17N3OS (M)+ 275.1092, found 275.1101. Anal. (C14H17N3OS) C, H, N.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe semi-solid residue was purified by silica gel (16×4 cm) chromatography
  4. customSolvents were evaporated
  5. dissolutionthe oily residue was redissolved in CHCl3/ether (1:1)
  6. filtrationFiltration and concentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a6cd37b12a7344838cf186a8387e9da9
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593330B2

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