Acetic Acid → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine
Reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[CH3:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[NH2:22].C(O)(=O)C.[BH4-].[Na+]>C(O)C.C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][NH:22][C:21]2[CH:23]=[C:24]([CH3:26])[CH:25]=[C:19]([CH3:18])[CH:20]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (15.0 mmol) in ethanol (44.6 mL) were added dropwise 3,5-dimethylaniline (15.8 mmol) and acetic acid (1.5 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature. After disappearance of the aldehyde was confirmed by gas chromatography, sodium borohydride (19.5 mmol) was added to the solution and reacted at room temperature for 3 hrs. Water and toluene were then added to the reaction mixture. The organic layer was dried and concentrated. The obtained oily substance was purified by silica gel column chromatography to give N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine (4.88 g, yield 73.3%) as a yellow oily substance.
Workup
- additionwas added to the solution
- customreacted at room temperature for 3 hrs
- customThe organic layer was dried
- concentrationconcentrated
- customThe obtained oily substance was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-621abfb3f9c24eee8afce0858cab84c9
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07439379B2
Reaction notes
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