Acetic Acid → HCID 10365615, 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 formaldehyde (8 μL, 0.1 mmol) in dichloroethane (2 mL) was stirred for 30 min at room temperature in the presence of 4A molecular sieves (200 mg). The reaction mixture was acidified with acetic acid (57 μL, 1.0 mmol), stirred for 16 h and treated with sodium triacetoxy borohydride (42.4 mg, 0.2 mmol). The resulting mixture was stirred at room temperature for 3 h and quenched with NaHCO3 (sat. 6 mL). 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 in vacuo. The residue was purified on SiO2 (20%–40%, EtOAc:Hexanes) to give 24.0 mg (55%) of the title compound.

Provenance & Evidence