Reaktion #499240

ord-5303cd42f8b647349761e54dab303ad8

Reaktionsgleichung

COC(=O)c1cccnc1Cl
methyl chloronicotinate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
c1cc(N2CCNCC2)ccn1
4-pyridylpiperazine
C1COCCOCCOCCOCCOCCO1
18-crown-6
COC(=O)c1cccnc1N1CCN(c2ccncc2)CC1
product
Ausbeute 82.0%
COC(=O)c1cccnc1N1CCN(c2ccncc2)CC1
Methyl 2-(4-(Pyrid-4-yl)piperazin-1-yl)nicotinate
Ausbeute 82.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe excess potassium carbonate was filtered off
  2. 2
    Einengenthe filtrate was concentrated
  3. 3
    Sonstigethe residue was partitioned between water and ethyl acetate
  4. 4
    TrocknenAfter drying the organic phase over magnesium sulfate
  5. 5
    Einengenconcentrating the solvent

Vorschrift

3.4 g of methyl chloronicotinate, 5.5 g of potassium carbonate, 3.3 g of 4-pyridylpiperazine and a spatula tipful of 18-crown-6 were heated at 100° C. for 5 h in 75 ml of DMF and then stirred at room temperature for 60 h. The excess potassium carbonate was filtered off, the filtrate was concentrated and the residue was partitioned between water and ethyl acetate. After drying the organic phase over magnesium sulfate and concentrating the solvent, 3.9 g (82%) of the product were obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06562827B1uspto-grants-2003_05