Dicyclohexylcarbodiimide → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-6-(methyloxy)benzamide

Participants

Reaction Steps

A mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (0.220 g, 1 mmol), 2-methoxy-6-methylbenzoic acid (0.200 g, 1.2 mmol), 1-hydroxybenzotriazole hydrate (0.183 g, 1.2 mmol) and PS-DCC (1 g of 1.3 mmol/g loading, 1.3 mmol) in DCM (10 ml) was stirred vigorously overnight. The mixture was washed with saturated aqueous sodium hydrogen carbonate, the layers separated through a phase separation cartridge and the organic layer applied to an SCX cartridge. The cartridge was eluted with DCM (×2), and then methanol (×2) followed by 1M ammonia in methanol. Evaporation of the solvent afforded the title compound which was characterised. 1H NMR (CDCl3) δ: 1.00-1.10 (1H, m), 1.25-1.40 (1H, m), 1.40-1.60 (2H, m), 1.60-1.80 (2H, m), 1.80-2.00 (2H, m), 2.24 (6H, s), 2.28 (3H, s), 3.80 (3H, s), 5.17 (1H, d, J=6 Hz), 6.75 (1H, d, J=8 Hz), 6.79 (1H, d, J=8 Hz), 7.10 (1H, br s), 7.15-7.30 (4H, m), 7.44 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 367 (MH+). C23H30N2O2 requires 366. Ret. time 1.92 min. The title product was converted to the corresponding hydrochloride salt (0.34 g, 85%).

Provenance & Evidence