13754-38-6, 13754-38-6 1-Benzoylpiperazine 762654, apiperazines compound, is more and more widely used in various fields.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13754-38-6,1-Benzoylpiperazine,as a common compound, the synthetic route is as follows.
General procedure: To a mixture of 1-benzoylpiperazine (1.0 eq) and potassium carbonate (2.0 eq) in dimethylformamide was added dropwise a solution of the corresponding substituted 9-bromo-9H-fluorene (1.0 eq) in dimethylformamide (The synthesis of 9-bromo-9H-fluorene derivatives is reported in supporting information). After stirring for 24 h at room temperature, solvent was removed and the crude residue was dissolved in diethyl ether, washed with brine, dried over magnesium sulfate,filtered and concentrated under vacuum. The residue was purified by flash chromatography as indicated in each case to afford the title compound. Reagents: 1-Benzoylpiperazine (0.16 mmol, 30 mg), potassium carbonate (0.31 mmol, 43 mg) and 9-bromo-2-octyl-9H-fluorene (0.16 mmol, 55 mg). The crude product was purified by flash chromatography (gradient, 100% petroleum ether to 100% ethyl acetate in 15 min) to afford a yellow oil (38 mg, 53%). TLC Rf: 0.10 (petroleum ether/ethyl acetate 90/10). IR (cm-1): 697, 708, 740, 765, 828, 1001, 1015, 1141, 1154, 1255, 1277, 1302, 1425, 1455, 1634, 1715, 2853, 2923. HPLC: method 2, rt = 7.63 min, purity 97%. 1H NMR (300 MHz, CDCl3) delta (ppm): 0.82-1.01 (m, 3H); 1.23-1.47 (m, 10H); 1.59-1.78 (m, 2H); 2.43 (s, 2H); 2.72 (t, J = 7.8 Hz, 2H); 2.92 (s, 2H); 3.38 (s, 2H); 3.85 (s, 2H); 4.88 (s, 1H); 7.23 (d, J = 7.8 Hz, 1H); 7.30 (td, J = 1.5 Hz, 7.5 Hz, 1H); 7.34-7.43 (m, 6H); 7.47 (s, 1H); 7.61 (d, J = 7.5 Hz, 1H); 7.63 (d, J = 7.5 Hz, 1H); 7.67 (d, J = 7.1 Hz, 1H). 13C NMR (75 MHz, CDCl3) delta (ppm): 14.2 (CH3); 22.7 (CH2); 29.3 (CH2); 29.4 (CH2); 29.5 (CH2); 31.8 (CH2); 31.9 (CH2); 36.2 (CH2); 43.0 (CH2); 48.4 (CH2); 48.5 (CH2); 49.7 (CH2); 69.9 (CH); 119.5 (CH); 119.6 (CH); 125.8 (CH); 125.9 (CH); 126.7 (CH); 127.1 (2 * CH); 128.3 (CH); 128.4 (2 * CH); 128.5 (CH); 129.6 (CH); 135.9 (C); 138.7 (C); 141.2 (C); 142.4 (C); 143.3 (C); 143.6 (C); 170.3 (C). MS (DCI/CH4) m/z: 467.31 [M+H+], 277.20 [M-189]. HRMS (DCI/CH4): for C32H39N2O [M+H+]: calcd: 467.3062; found: 467.3063.
13754-38-6, 13754-38-6 1-Benzoylpiperazine 762654, apiperazines compound, is more and more widely used in various fields.
Reference:
Article; Chollet, Aurelien; Mori, Giorgia; Menendez, Christophe; Rodriguez, Frederic; Fabing, Isabelle; Pasca, Maria Rosalia; Madacki, Jan; Kordulakova, Jana; Constant, Patricia; Quemard, Annaik; Bernardes-Genisson, Vania; Lherbet, Christian; Baltas, Michel; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 218 – 235;,
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