1-Benzyl-4-(ethylamino)piperidine-4-carboxamide → 4-(Ethylamino)piperidine-4-carboxamide
Reaktionsgleichung
C([N:8]1[CH2:13][CH2:12][C:11]([NH:17][CH2:18][CH3:19])([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:18]([NH:17][C:11]1([C:14]([NH2:16])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH3:19]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 1-benzyl-4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1f; 7.39 g, 28.3 mmol) in methanol (100 ml) was added 20% Pd(OH)2 on carbon (50% water; 1.48 g). The mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature overnight. The mixture was filtered through a pad of Celite®, and then concentrated to give a colorless solid I-1A-1g (4.84 g, quantitative): +APcI MS (M+1) 172.2; 1H NMR (400 MHz, CD2Cl2) δ 2.89 (ddd, J=12.9, 8.7, 3.3 Hz, 2H), 2.75 (ddd, J=12.9, 6.6, 3.7 Hz, 2H), 2.45 (q, J=7.2 Hz, 2H), 1.95 (ddd, J=13.7, 8.3, 3.7 Hz, 2H), 1.55 (ddd, J=13.7, 6.6, 3.3 Hz, 2h), 1.08 (t, J=7.1 Hz, 3H).