4-(Prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole → 4-(Propyl)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole
Reaction equation
[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:29][CH2:30]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 50 ml sinfle neck round bottom flask, under a nitrogen atmosphere, 4-(prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole (100 mg, 0.19 mmol) was added to ethyl acetate (4 ml). To this solution was added 10% palladium on activated carbon (100 mg), followed by the addition of a hydrogen balloon. The reaction mixture was stirred for three hours at room temperature, then filtered through a bed of CELITE™. The desired title product was further purified by radial chromatography.
Workup
- filtrationfiltered through a bed of CELITE™
- customThe desired title product was further purified by radial chromatography
Sources & evidence
- ORD record
- ord-1b1a4f76263e4e018402dc711b28c71b
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06255494B1
Reaction notes
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