2-Chloronicotinonitrile → tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 645667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645667
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])O.[K+]>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Komponenten

5

Edukt 3

HCID 810792-ChloronicotinonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516893Potassium Bicarbonate

Produkt 1

HCID 22061422tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Chloro-nicotinonitrile (2.04 g, 14.7 mmol) was added to a mixture of piperazine-1-carboxylic acid tert-butyl ester (2.74 g, 14.7 mmol) and potassium hydrogencarbonate (1.77 g, 17.6 mmol) in N,N-dimethylformamide (45 mL). The mixture was heated at 90° C. overnight. The solvent was removed and residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed to give the titled compound as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 8.428 (dd, 1H); 8.08 (dd 1H); 6.95 (dd, 1H); 3.58 (m, 4H); 3.47 (m, 4H); 1.42 (s, 9H).

Aufarbeitung

  1. customThe solvent was removed
  2. customresidue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-8b76c43a772a4f89aa7ba993427d3be0
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704997B1

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