Benzene, 1-bromo-3-(trifluoromethyl)- → 1-[3-(Trifluoromethyl)phenyl]piperidin-4-ol

Temperature

100 °C

A mixture of 1-bromo-3-(trifluoromethyl)benzene (6.13 mL, 44.44 mmol), piperidin-4-ol (5.608 g, 55.44 mmol), diacetoxypalladium (0.200 g, 0.89 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.553 g, 0.89 mmol) and cesium carbonate (18.10 g, 55.55 mmol) in dioxane (100 mL) was evacuated and backfilled with N2 three times and then it was heated at 100 °C for 6h. The mixture was filtered through filter agent(supercell), washed with EtOAc. The combined filtrate was concentrated. The residue was purified by silica gel column(0-35% EtOAc/hexane) to give 1-(3-(trifluoromethyl)phenyl)piperidin-4-ol (4.70 g, 43.1 %) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) d 7.38 (t, _J_ = 8.03 Hz, 1H), 7.20 (dd, _J_ = 2.38, 8.41 Hz, 1H), 7.13 (s, 1H), 7.00 (d, _J_ = 7.78 Hz, 1H), 4.64 - 4.72 (m, 1H), 3.53 - 3.72 (m, 3H), 2.93 (ddd, _J_ = 3.01, 9.98, 12.86 Hz, 2H), 1.71 - 1.88 (m, 2H), 1.45 (dtd, _J_ = 3.89, 9.44, 12.86 Hz, 2H). LCMS 246.

ORD record

ord-9afd80193ebe4d909351826d5e746d73

Source dataset

750 AstraZeneca ELN dataset

Original link

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