Reaktionsgleichung
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:8][NH2:9])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:4][CH2:3]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 1-methyl-4-(pyridin-2-yl)piperidine-4-carbonitrile (0.544 g, 2.70 mmol) in tetrahydrofuran (10 mL) was slowly added to a suspension of lithium aluminum hydride (0.205 g, 5.41 mmol) in tetrahydrofuran (10 mL) at 23° C. The reaction was stirred overnight, then quenched with sodium sulfate decehydrate. This was stirred for 1 hour, then ethyl acetate was added and the slurry was stirred for 2 more hours. Celite was added and the paste was filtered on Celite. The filtrate was concentrated to afford an oil (0.518 g, 93%) which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 1.76-1.88 (2H, m), 2.07-2.19 (2H, m), 2.23 (3H, s), 2.43 (2H, br d, J=14.6 Hz), 2.58-2.69 (2H, m), 2.87 (2H, s), 7.16 (1H, ddd, J=7.52, 4.86 and 1.01 Hz), 7.33 (1H, d, J=8.08 Hz), 7.69 (1H, td, J=7.77 and 1.89 Hz), 8.65 (1H, d, J=4.80 and 1.01 Hz).
Aufarbeitung
- customquenched with sodium sulfate decehydrate
- stirringThis was stirred for 1 hour
- additionethyl acetate was added
- stirringthe slurry was stirred for 2 more hours
- additionCelite was added
- filtrationthe paste was filtered on Celite
- concentrationThe filtrate was concentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-2bb1beb1e3d74cb5987c20cd3b3ff99d
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08343999B2
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