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acridin-9-yl-[4-(piperidin-1-yl)phenyl]amine[ No CAS ]
[ 2359-60-6 ]
Yield
Reaction Conditions
Operation in experiment
6%
Following the procedure outlined in Step 2 of Example 1, but substituting 4-piperidin-1-yl-1-nitrobenzene for 1-methyl-4-(4-nitrophenyl)piperazine, afforded 4-piperidin-1-ylaniline, which was reacted with 9-chloroacridine (according to Step 4 in the procedure of Example 1) to obtain the title compound with 6% overall yield. 1H NMR (CDCl3, 500 MHz): 8.05 (2H, m), 8.00 (2H, m), 7.48 (2H, m), 7.09 (4H, m), 6.86 (2H, m), 3.13 (4H, m), 1.71 (4H, m), 1.58 (2H, m); MS (ESI+TOF): 354 (M+)
N-(acridin-9(10H)-ylidene)naphthalene-1-sulfonimide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 20 - 80℃; for 14h;Inert atmosphere;
General procedure: A dry round bottom flask was cooled to rt under nitrogen, and was charged with Pd2(dba)3 (3.38mg, 0.0037mmol), cesium carbonate (361mg, 1.11mmol), and arenesulfonamide (69mg, 0.44mmol). Tertiary-butanol (2mL) was added, followed by ligand, xantphos (6.4mg, 0.011mmol) and 9-chloroacridine (80mg, 0.37mmol). The resulting suspension was stirred at rt for 5min, then heated to 80C for 12-17h. The reaction mixture was then cooled to rt and filtered through suction filtration. The organic fraction was evaporated, and the resulting residue was purified by silica gel chromatography with a hexane/Et-OAc as eluent (60:40).
With [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; sodium carbonate; In water; toluene; at 60℃; for 5h;
In a 250 mL three-necked flask, 21.4 g (0.1 mol) of 9-chloroacridine, 18.0 g (0.11 mol) of <strong>[216019-28-2]3-isopropylphenylboronic acid</strong>, 0.11 g of PdCl2 (dppb) catalyst, 100 g of toluene, and 2 g of sodium carbonate were sequentially added. 18 g of deionized water, heated to 60 C., reacted for 5 hours, cooled to 25 C., removed the solvent by rotary evaporation, washed with 100 g of methanol and dispersed, and filtered to obtain a crude product. The crude product was refined with 80 g of toluene and dried to obtain 28.9 g of the product in a yield 97.3%, HPLC content 99.57%.
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