Acetic Acid → HCID 9981094, compound

Participants

Reaction Steps

A solution of 3-(5-Fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) and the formaldehyde (1.49 ml, 20 mmol) in acetonitrile (2 ml) was stirred for 30 minutes at room temperature. The reaction mixture was acidified with acetic acid (57 μL, 1.0 mmol) and treated with sodium cyanoborohydride (31.4 mg, 0.5 mmol). The resulting mixture was stirred at room temperature for 15 h and quenched with NaHCO3 (sat. 2 ml). Phases were separated and the aqueous layer was extracted with CHCl3 (3×2ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was dissolved in Et2O and treated with HCl (2M in Ether) until the mixture was acidic (pH˜2). The ether layer was decanted and the salt was washed with ether (5×2 ml) and dried. The solid was dissolved in CHCl3, extracted with NaHCO3 (sat.), phases were separated and the aqueous layer was extracted with CHCl3 (2×4 ml). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified on SiO2 (20%–30%, EtOAc: Hexanes) to give 12.5 mg (28%) of the title compound.

Provenance & Evidence