Dicyclohexylcarbodiimide → 2-Bromo-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-6-methylbenzamide

Beteiligte Stoffe

Reaktionsschritte

To {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (50 mg, 0.23 mmol) in DCM (5 ml) was added 2-bromo-6-methylbenzoic acid (108 mg; 0.5 mmol), followed by 1-hydroxybenzotriazole (45 mg; 0.3 mmol) and PS-DCC (400 mg of 1.3 mmol/g loading, 0.52 mmol) and the mixture shaken at room temperature for ca. 2 days. The reaction mixture was filtered through a phase-separation cartridge and the filtrate stirred with saturated aqueous sodium bicarbonate for 30 min. The lower layer was removed, passed through another phase-separation cartridge and loaded onto an SCX cartridge which was eluted with 2 column volumes each of DCM, 50% methanol-DCM, methanol and 1M ammonia in methanol. The product containing fractions were evaporated to afford the title product (82 mg; 82%). 1H NMR (CDCl3) δ: 0.95-1.10 (2H, m), 1.40-1.60 (2H, m), 1.60-1.80 (2H, m), 1.80-1.90 (2H, m), 2.23 (6H, s), 2.33 (3H, m), 5.13 (1H, d J=6 Hz), 6.97 (1H, br s), 7.10-7.15 (2H, m), 7.24-7.34 (3H, m), 7.38-7.41 (1H, m), 7.46-7.48 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 415 (MH+). C22H2779BrN2O requires 414. Ret. time 1.93 min.

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