Sodium Hydroxide → 4-(4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-yl)morpholine

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Reaction Steps

The product from previous reaction 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine (4.7 g, 11.03 mmol) was stirred in 6M sodium hydroxide (100 mL, 600 mmol) solution with 1-bromo-2-(2-bromoethoxy)ethane (6.87 mL, 55.1 mmol) and tetrabutylammonium iodide (0.407 g, 1.103 mmol) at 110° C. After stirring for 2.5 hr the mixture was cooled and the aqueous was decanted and the remaining sticky solid was dissolved in EtOAc. The organic was washed with H2O and brine and dried over MgSO4 and concentrated to leave a thick dark residue containing the desired product. The desired product was purified by flash chromatography on a silica column eluting with EtOAc/Hex 15% to 40% over 20 column volumes. The fractions containing the desired compound by TLC were combined and concentrated to provide 4-(4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-yl)morpholine (2.75 g, 4.99 mmol, 45.2% yield) as a light orange solid. MS (ES+) m/e: 495.1, 496.1 [M+H]+

Provenance & Evidence