Aniline → HCID 58897808, compound

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Reaction Steps

Under an argon atmosphere, to a solution of 4.56 ml (4.66 g, 50.0 mmol) of PhNH2 in 200 ml of toluene, 20.0 ml of 2.5 M nBuLi (50.0 mmol) in hexanes was added dropwise at ambient temperature. Then, hexanes were distilled off under vacuum. To the obtained suspension, 12.1 g (39.7 mmol) of 4-bromo-1-methoxy-1-phenylindane, 434 mg (0.76 mmol) of Pd(dba)2, and 503 mg (1.47 mmol) of N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine were added. This mixture was refluxed for 1 hour, then, 300 ml of water was added. The organic layer was separated; the aqueous layer was extracted with 3×75 ml of ether. The combined extract was dried over Na2SO4 and, then, evaporated to dryness. The analytically pure 1-methoxy-N,1-diphenyl-4-indanamine was obtained by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1300 mm, eluant: CH2Cl2). Yield, 12.5 g (99%).

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