2-Chloro-4-cyanopyridine → 2-(4-Cyclopentyl-piperazin-1-yl)-isonicotinonitrile

HRID 1432143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432143
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[CH:10]1([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11]1>CN(C=O)C>[CH:10]1([N:15]2[CH2:16][CH2:17][N:18]([C:2]3[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=3)[C:8]#[N:9])[CH2:19][CH2:20]2)[CH2:11][CH2:12][CH2:13][CH2:14]1

Komponenten

4

Edukt 2

HCID 5686382-Chloro-4-cyanopyridineHCID 8064211-Cyclopentylpiperazine

Produkt 1

HCID 623696172-(4-Cyclopentyl-piperazin-1-yl)-isonicotinonitrileAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2 g (14 mmol) 2-chloro-4-cyanopyridine and 2.34 g (15 mmol) 1-cyclopentylpiperazine in 5 ml DMF was heated to 80° C. for 16 h. The mixture was evaporated under reduced pressure and the residue was treated with 100 ml 1M NaHCO3 aq. and extracted with two times 100 ml ethyl acetate. The combined organic phases were dried with MgSO4 and evaporated under reduced pressure to yield 3.4 g (92%) of the title compound as grey solid. (m/e): 257.3 (MH+; 100%).

Aufarbeitung

  1. customThe mixture was evaporated under reduced pressure
  2. additionthe residue was treated with 100 ml 1M NaHCO3 aq.
  3. extractionextracted with two times 100 ml ethyl acetate
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c2a616dd5123415b9c3872b27ebc6fa6
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612076B2

Notizen zur Reaktion

Wird geladen…