[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone → [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone
Reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:26]4[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][CH2:19][CH2:18]3)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:26]4[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][CH2:19][CH2:18]3)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1Participants
4
Procedure
To a solution of [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.8 g, 0.0051 mol) in methanol (10 mL) was added 10% Pd/C (0.2 g). The reaction mixture was hydrogenated at 3 kg pressure for 2 h. The catalyst was filtered over celite and the filtrate was concentrated to give [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.5 g, 90%).