Hydrochloric Acid → 6-(4-Aminopiperidin-1-yl)pyridine-3-carbonitrile
Reaktionsgleichung
Cl.[C:2]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([NH:16]C(=O)C)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)#[N:3].[OH-].[Na+]>>[NH2:16][CH:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][N:8]=2)[CH2:11][CH2:12]1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
2N HCl (3 mL) was added to N-(1-(5-cyanopyridin-2-yl)piperidin-4-yl)acetamide (300 mg, 1.22 mmol) and the reaction mixture was stirred at 100° C. for 5 h. The reaction mixture was cooled to room temperature and the pH of the aqueous layer was adjusted to 8-9 using 10% NaOH solution. The product was extracted with CH2Cl2 and the combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 6-(4-aminopiperidin-1-yl)nicotinonitrile (210 mg, crude), which was carried through without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.43 (d, J=2.3 Hz, 1H), 7.79-7.75 (dd, J=9.1 Hz, 2.3 Hz, 1H), 6.90 (d, J=9.2 Hz, 1H), 4.28-4.23 (m, 2H), 3.07-2.98 (m, 2H), 2.87-2.78 (m, 1H), 1.75-1.71 (m, 2H), 1.19-1.07 (m, 2H). MS (ESI) m/z: Calculated for C11H14N4: 202.12. found: 203.2 (M+H)+