Trifluoroacetic acid → 2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl-methyl amine

Participants

Reaction Conditions

Reaction Steps

Entire reaction was performed under argon atmosphere using syringe septa technique. {2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (1.578 mmol, 1 eq) was dissolved in dichloromethane (6 ml) and stirred at 0° C. for 5 min. TFA (15.778 mmol, 10 eq) was added and stirring was continued for 50 hours. Reaction mixture was diluted with 50 ml NaHCO3 (sat.) and extraction with DCM (3×20 ml) followed. Organic layers were combined and evaporated. Crude product was put on a previously conditioned SCX column (5 g). Column was washed with MeOH (2×10 ml) and then with 2M NH3/MeOH to retrieve the product, {2-[4-(4-fluoro-phenoxy)-phenyl]ethyl}-methyl-amine (1.468 mmol, yield=93%, purity=94%). [M+H]+=246.22 1H NMR (300 MHz, CDCl3) δ/ppm 2.43 (s, 3H), 2.72-2.86 (m, 4H), 6.84-7.03 (m, 5H), 7.10-7.17 (m, 2H), 7.24 (s, 1H)

Provenance & Evidence