2,6-Dichlorobenzoic acid → (+/-)-2,6-Dichloro-N-[[1-(dimethylamino)cyclopentyl] (phenyl)methyl]benzamide

Participants

Reaction Steps

To a solution of 2,6-dichlorobenzoic acid (20 mg; 0.105 mmol) in DCM (2 ml) and N-methylpyrrolidinone (0.1-0.5 ml) was added 1-hydroxybenzotriazole (18 mg; 0.11 mmol) and PL-dicyclohexylcarbodiimide (88 mg; 0.14 mmol; Polymer Labs 1.59 mmol/g). The mixture was shaken at room temperature for 1 hour and then 1-[amino(phenyl)methyl]cyclopentyl}dimethylamine dihydrochloride D2 (20 mg; 0.07 mmol) and PS-diisopropylethylamine (82 mg; 0.21 mmol; Polymer Labs 2.59 mmol/g) were then added and shaking continued overnight at room temperature. An excess of PS-Trisamine was then added and after shaking for a further 4 h, the mixture was filtered and the resins washed well with DCM and methanol. The filtrate was reduced in volume by evaporation in vacuo and loaded onto an SCX cartridge (500 mg). Washing with DCM, then methanol followed by elution with 1M ammonia in methanol afforded the title product (22.8 mg). 1H NMR (CDCl3) δ: 0.98 (1H, m), 1.26 (1H, m), 1.40 (2H, m), 1.68 (2H, m), 1.85 (2H, m), 2.22 (6H, s), 5.08 (1H, bs), 7.27 (7H, m), and 7.47 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 391 (MH+). C21H2435Cl2N2O requires 390. Ret. time 1.88 min.

Provenance & Evidence