Benzyl Bromide → 1-Benzyl-4-(2-trifluoromethoxy-phenyl)-1,2,3,6-tetrahydro-pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-trifluoromethoxy-phenyl)-pyridine in toluene was added (1 eq.) benzyl bromide, and reaction mixture was stirred under reflux for 2 h. Reaction was monitored by TLC (CH2Cl2/MeOH 95:5) and revealed total conversion to the first intermediate. Complete evaporation of solvent gave a white solid which was pure enough to carry out the next step. The white solid was dissolved in MeOH under argon and cooled down to 0° C., (4 eq.) NaBH4 was added portion-wise (exothermic reaction). The reaction mixture was then stirred for 3 h at RT, reaction again monitored by TLC (CH2Cl2/MeOH 95:5) and revealed total conversion. Evaporation of MeOH, redissolution in CH2Cl2, and washing with 1N NaHCO3 then brine, and evaporation, followed by SiO2 gel chromatography (CH2Cl2/MeOH) gave the title compound in 61% yield.

Provenance & Evidence