Triethylamine → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2,6-dimethyl benzamide

Beteiligte Stoffe

Reaktionsschritte

A solution of 2,6-dimethylbenzoyl chloride (1.7 g, 10.1 mmol) in DCM (10 ml) was added dropwise to a mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (2.0 g, 9.2 mmol), and triethylamine (1.4 ml, 10.0 mmol) in DCM (40 ml) and stirred at room temperature for 2 h. The mixture was washed with saturated aqueous sodium hydrogen carbonate, the organic layer was separated through a phase separation cartridge and then evaporated to a white solid. Chromatography with eluent 50-100% ethyl acetate/pentane, then 0-10% methanol/ethyl acetate afforded the title product as a white solid (3.1 g, 97%). 1H NMR (CDCl3) δ: 0.85-1.00 (1H, m), 1.30-1.55 (3H, m), 1.60-1.75 (2H, m), 1.78-1.90 (2H, m), 2.21 (6H, s), 2.31 (6H, s), 5.19 (1H, d, J=6 Hz), 6.79 (1H, br d), 7.02 (2H, d, J=8 Hz), 7.16 (1H, t, J=8 Hz), 7.20-7.35 (3H, m), 7.43 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 351 (MH+). C23H30N2O requires 350. Ret. time 2.0 min. The white solid product was converted to the HCl salt using 1M HCl/diethylether to afford the salt as a white solid on evaporation.

Herkunft & Nachweise