Formaldehyde → HCID 69266287, compound

Participants

Reaction Steps

Sodium cyanoborohydride (0.55 g, 14.1 mmol) is added to a stirred mixture of paraformaldehyde (0.82 g, 27.3 mmol) and 2-[(4-pyridyl)methyl]amino-N-[3-(trifluoromethyl)phenyl]benzamide (Example 14; 1.03 g, 2.78 mmol) in tetrahydrofuran (30 mL) at 20° C. under an argon atmosphere. The resulting mixture is then treated dropwise with trifluoroacetic acid (15 mL) and stirred at room temperature for 20 hours. The mixture diluted with ice-cold aqueous sodium hydroxide (100 mL of 5M) and extracted with dichloromethane (3×100 mL). The organic phase is dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate, to give the title compound as a colourless crystalline solid.

Provenance & Evidence