With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59878-57-8,1-(Cyclopropylcarbonyl)piperazine,as a common compound, the synthetic route is as follows.
To a round bottom flask was added, 2-fluorobenzoic acid (1.00 g, 7.14 mmol), DCM (40 mL), diisopropylethylamine (1.86 mL, 10.7 mmol) and HBTU (4.06 g, 10.7 mmol). The reaction mixture was then stirred for 30 minutes at room temperature before adding cyclopropylpiperazine-l-ylmethanone (1.52 mL, 10.7 mmol). The reaction was stirred overnight before the excess solvent with removed in vacuo and the cmde material purified via flash column chromatography (EtOAc:MeOH 10:1) affording (4- (Cyclopropanecarbonyl)piperazin-l-yl)(2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanone as a white solid (1.32 g, 4.78 mmol 67%) in a mixture of rotamers (2:1). In each case the shift relating to the minor rotamer has been donated with an asterisk.* NMR (400 MHz, CDCh) d = 7.40 – 7.29 (m, 2H + 2H*), 7.16 (td, / = 7.5, 1.1 Hz, 1H + 1H*), 7.04 (ddd, J = 9.4, 8.3, 1.1 Hz, 1H + 1H*), 3.88 – 3.46 (m, 6H + 6H*), 3.38 – 3.20 (m, 2H + 2H*), 1.76 – 1.58 (m, 1H + 1H*), 0.98 – 0.88 (m, 2H + 2H*), 0.83 – 0.62 (m, 2H + 2H*); 13C NMR (100 MHz, CDCb) d = 172.3 (1C + 1C*), 165.4 (1C + 1C*), 158.0 (d, 7 = 247.7 Hz, 1C + 1C*), 131.7 (d, 7 = 8.0 Hz, 1C + 1C*), 129.1 (1C + 1C*), 124.9 (d, 7 = 3.5 Hz, 1C + 1C*), 123.5 (d, 7 = 17.4, 1C + 1C*), 115.8 (d, 7 = 21.3, 1C + 1C*), 47.0 (1C*), 46.7 (1C), 45.6 (1C*), 45.1 (1C), 42.2 (2C), 41.9 (1C*), 41.7 (1C*), 11.0 (1C + 1C*), 7.64 (2C + 2C*); OH^F NMR (376 MHz, CDCb) d = – 115.0 (s, IF*), – 115.1 (s, IF); IR (v, cm x): 1630, 1460, 1219, 1004, 727; HRMS (ESI) for Ci5Hi819FN202 [M+H]+ requires 277.1282 found 277.1285; Mp: 65 – 67C., 59878-57-8
The synthetic route of 59878-57-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GOUVERNEUR, Veronique; CORNELISSEN, Bart; WILSON, Thomas Charles; (152 pag.)WO2019/186135; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics