CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(NC(C)=O)cc1Br>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.[Na+].[Pd]>COc1ccc(NC(C)=O)cc1N1CCNCC1
A solution of N-(3-bromo-4-methoxyphenyl)acetamide (0.5 g, 2.05 mmol) dissolved in toluene (5 mL) was treated with tert-butyl piperazine-1-carboxylate (0.382 g, 2.05 mmol), diacetoxypalladium (0.046 g, 0.20 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.191 g, 0.41 mmol) and sodium 2-methylpropan-2-olate (0.433 g, 4.51 mmol) in a sealed tube. The resulting mixture was degassed and stirred at 100 °C for 8 hours in a microwave. The mixture was pre-absorbed onto silica. The crude product was purified by flash silica chromatography, elution 50% ethyl acetate in Heptane. Pure fractions were evaporated to dryness to afford intermediate. The intermediate was dissolved in 4M HCl in dioxane (10mL) and stirred at RT overnight. The mixture was evaporated to give N-(4-methoxy-3-(piperazin-1-yl)phenyl)acetamide (0.260 g, 50.9 %) as a tan solid.
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