With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-78-2,tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.
To a stirred solution of 3-bromobiphenyl (0.70 g, 3.00 mmol) in toluene (10 mL) was added t-butyl 2-methylpiperazine-l-carboxylate (0.720 g, 3.60 mmol), potassium t- butoxide (0.504 g, 4.50 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.090 g, 98.3 mmol) and tri-t-butylphosphine (0.018 g, 89.0 mmol). The mixture was heated at 90 C for 5 hours. At this time the reaction was cooled, diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The residue was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford t-butyl 4-([l, -biphenyl]-3-j/j-2-methylpiperazine- 1-carboxylate (0.750 g, 71%) as a brown oil. The t-butoxycarbonyl protecting group was removed from this compound using General Procedure G to afford l-([l,l’-biphenyl]-3- yl)-3-methylpiperazine. This intermediate was, in turn, was reacted with Intermediate 5 using General Procedure A to generate the title compound. 1H NMR (500 MHz, CDCI3) delta 7.60-7.34 (m, 6H), 7.12-7.11 (m, 2H), 6.92-6.90 (m, 1H), 4.40-4.39 (d, J= 6.5 Hz, 1H), 4.19-4.14 (m, 1H), 3.87-3.33 (m, 4H), 3.09-2.88 (m, 8H), 2.46-2.43 (m, 1H), 1.99-1.55 (m, 9H), 1.38 (t, J = 7.0 Hz, 3H) ppm. 13C NMR (125 MHz, CDC13) delta 156.7, 156.7, 151.9, 142.5, 141.6, 129.5, 128.7, 127.3, 127.2, 119.1, 115.4, 115.4, 115.3, 115.3, 59.0, 54.3, 54.3, 53.2, 53.3, 49.1, 49.1, 47.9, 47.8, 47.7, 47.7, 46.1, 46.0, 39.8, 39.5, 39.1, 39.0, 36.7, 36.4, 25.9, 25.8, 25.4, 24.3, 24.3, 24.1, 24.0, 15.8, 15.7 ppm. Purity: >99% (214 & 254 nm) LCMS; retention time: 1.29 min; (M+H+) 433.3
120737-78-2, The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GENZYME CORPORATION; BOURQUE, Elyse; CABRERA-SALAZAR, Mario, A.; CELATKA, Cassandra; CHENG, Seng, H.; HIRTH, Bradford; GOOD, Andrew; JANCSICS, Katherine; MARSHALL, John; METZ, Markus; SCHEULE, Ronald, K.; SKERLJ, Renato; XIANG, Yibin; ZHAO, Zhong; LEONARD, John; NATOLI, Thomas; MAKINO, Elina; HUSSON, Herve; BESKROVNAYA, Oxana; WO2014/43068; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics