Dicyclohexylcarbodiimide → 4-Chloro-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-2-methylbenzamide

Participants

Reaction Steps

A mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (80 mg, 0.37 mmol), 4-chloro-2-methylbenzoic acid (68 mg; 0.40 mmol), HOBt (61 mg; 0.40 mmol) and PS-DCC (310 mg of 1.3 mmol/g loading, 0.40 mmol) in DCM (4 ml) was shaken overnight. Saturated aqueous sodium bicarbonate was added and the mixture separated with a phase-sep cartridge and the organics applied directly to SCX resin. Elution with DCM, methanol and then 1M ammonia in methanol, followed by chromatography eluting with 12-100% ethyl acetate-pentane (SP4 Biotage) afforded the title product (64 mg; 43%). 1H NMR (CDCl3) δ: 0.9-1.0 (1H, m), 1.25-1.40 (1H, m), 1.4-1.6 (2H, m), 1.6-1.75 (2H, m), 1.8-1.9 (2H, m), 2.22 (6H, s), 2.41 (3H, s), 5.09 (1H, d, J=5 Hz), 7.07 (1H, d, J=5 Hz), 7.2-7.4 (8H, m). Mass Spectrum (Electrospray LC/MS): Found 371 (MH+). C22H2735ClN2O requires 370. Ret. time 2.26 min. The title product was converted to the corresponding hydrochloride salt.

Provenance & Evidence