[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>ClCCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:17]([CH:14]2[CH2:16][CH2:15]2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
To a mixture of 1-benzyl-piperazine (1.20 g, 6.81 mmol) in anhydrous DCE (23 mL) was added cyclopropane carboxylic acid chloride (854 mg, 8.17 mmol, 1.2 eq) followed by diisopropylethylamine (1.3 mL, 7.49 mmol, 1.1 eq), and the reaction mixture was stirred at 50° C. under N2 for 15 h. The mixture was cooled to rt and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (Biotage®, gradient elution 75% EtOAc/hexane) to give the product (1.65 g, 99%) as a brown oil. 1H-NMR (300 MHz, DMSO-d6) 7.34 to 7.23 (m, 5H), 3.64 (broad s, 2H), 3.48 (s, 2H), 3.44 (broad s, 2H), 2.37 (broad s, 2H), 2.28 (broad s, 2H), 1.95 to 1.91 (m, 1H), 0.70 to 0.65 (m, 4H); ES-MS m/z 245.2 [M+H]+, RT (min) 1.12.
Wird geladen…
