Triethylamine → HCID 58010777, compound

Participants

Reaction Steps

(R)-α-hydroxyisocaproic acid (52.1 g, 0.394 mol) was added to a solution of 1-benzylpiperazine (69.46 g, 0.394 mol) in CH2Cl2 (500 mL). The mixture was cooled in ice and Et3N (57 mL, 0.5 mol) was added, followed by HOBt (53.25 g, 0.394 mol) and EDCI.HCl (76.0 g, 0.396 mol). The reaction mixture was allowed to warm to room temperature overnight. The organic layer was washed with water (3×200 mL). The combined aqueous layers were back-extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with water (3×20 mL), dried over Na2SO4 and concentrated to give 1-(4-benzyl-piperazin-1-yl)-2-(R)-hydroxy-4-methyl-pentan-1-one as a brown oil (109 g, 0.375 mol, 95%). 1H NMR (300 MHz, CDCl3): d 7.35-7.24 (m, 5H); 4.35 (dd, J=10 Hz, 2 Hz, 1H); 3.77-3.55 (m, 4H); 3.52 (s, 2H); 3.36 (m, 2H); 4.45 (m, 4H); 1.97 (m, 1H); 1.47-1.38 (m, 1H); 1.29-1.21 (m, 1H); 0.96 (d, J=6 Hz, 3H); 0.94 (d, J=6 Hz, 3H) ppm.

Provenance & Evidence