Category: 31166-44-6

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In 35 mL of N,N-dimethylformamide were dissolved benzyl 1-piperazinecarboxylate (5.00 g, 22.7 mmol) and cyclopropanecarboxylic acid (2.54 g, 29.5 mmol), and 1-ethyl-3-(3-(N,N-dimethylamino)propyl)-carbodiimide hydrochloride (6.53 g, 34.1 mmol), 1-hydroxybenzotriazole (4.52 g, 29.5 mmol) and triethylamine (3.60 g, 35.9 mmol) were added thereto at room temperature, followed by stirring at the same temperature for three hours. The reaction mixture was mixed with water, and extracted twice with ethyl acetate. The organic layer was sequentially washed with water twice, with a saturated aqueous solution of sodium bicarbonate once and with brine once, and then dried over anhydrous sodium sulfate. The organic layer was passed through a silica gel column (Fuji Silysia, NH Silica gel) and evaporated to give the title compound (6.10 g, 93.1percent) as a white amorphous.1H-NMR Spectrum (CDCl3,400MHz) delta(ppm): 0.75-0.83(2H,m), 0.95-1.03(2H,m),1.65-1.75(1H,m),3.40-3.80(8H,m),5.16(2H,s), 7.30-7.40(5H,m)., 31166-44-6

As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

Reference：
Patent; MERCIAN CORPORATION; Eisai Co., Ltd.; EP1508570; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

Benzyl piperazine-1-carboxylate (1.00 g, 4.54 mmol) and K2CO3 (1.255 g, 9.08 mmol) were dissolved in acetonitrile (12.87 ml) to form a suspension. 1-bromo-2-chloroethane (2.3 ml, 27.24 mmol) was added to the reaction mixture at r.t and the resulting mixture was stirred at this temperature for 96 hours.The reaction mixture was filtered, and the filtrate concentrated under reduced pressure.Purification by column chromatography (ISCO, silica gel column, eluting with 0?100percent EtOAc in hexanes) gave the title compound (0.64 g, yield: 50percent).1H NMR (300 MHz, CHLOROFORM-d) d ppm 7.28-7.43 (m, 5H) 5.15 (s, 2H) 3.48-3.65 (m, 6H) 2.76 (t, 2H) 2.42-2.57 (m, 4H).LCMS: (ESI) m/z 283 [M+H]+.

31166-44-6, The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; US2012/35134; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

Benzyl piperazine-1-carboxylate (1.00 g, 4.54 mmol) and K2CO3 (1.255 g, 9.08 mmol) were dissolved in acetonitrile (12.87 ml) to form a suspension. 1-bromo-2-chloroethane (2.3 ml, 27.24 mmol) was added to the reaction mixture at r.t and the resulting mixture was stirred at this temperature for 96 hours.The reaction mixture was filtered, and the filtrate concentrated under reduced pressure.Purification by column chromatography (ISCO, silica gel column, eluting with 0?100percent EtOAc in hexanes) gave the title compound (0.64 g, yield: 50percent).1H NMR (300 MHz, CHLOROFORM-d) d ppm 7.28-7.43 (m, 5H) 5.15 (s, 2H) 3.48-3.65 (m, 6H) 2.76 (t, 2H) 2.42-2.57 (m, 4H).LCMS: (ESI) m/z 283 [M+H]+.

31166-44-6, The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; US2012/35134; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of bromide 61 (180 mg, 0.5 mmol), Cu20 (8 mg, 0.1 eq.) and 1 -Z-piperazine (0.5 mL, 2.5 mmol) in water (1 .0 mL) was stirred in a seal tube at 100 °C for 18 h. The reaction was cooled and the residue was extracted with EtOAc (3 x 25 mL). The combined organic layers were dried on MgS04, filtered and concentrated in vacuo. The crude reaction mixture was purified by flash column chromatography on silica gel [DCM/MeOH (2percent MeOH)] to give 89 as colourless solid (220 mg, 89percent), which was used in the next step without further purification. (0603) 1H NMR (500 MHz, CDCU, deltaEta): 7.37-7.30 (m, 5H, Ar), 5.74 (d, J = 2.5 Hz, 1 H, C3-H), 5.64 (s, 1 H, C5-H), 5.16 (s, 2H, CH2-Ph), 4.39-4.06 (m, 3H, C7-H, C1 1 -H, C12-H), 3.77 (dd, J = 15.0, 6.0 Hz, 1 H, C7-H), 3.60 (m, 4H, C13-H), 3.27 (m, 4H, C14-H), 3.01 (m, 2H, C1 1 -H C12-H), 2.87 (s, 1 H, C10-H), 2.35 (s, 1 H, C8-H), 1 .97 (d, J = 12.5 Hz, 1 H, C9-H), 1 .89 (d, J = 12.5 Hz, 1 H, C9-H), 1 .40-1 .18 (s, 9H, Boc); 13C NMR (125 MHz, CDCI3, 5C): 164.3 (CO), 156.4 (CO), 155.1 (CO), 154.6 (C4), 148.3 (C6), 136.4 (Ar), 128.5 (2C, Ar), 128.1 (Ar), 127.9 (2C, Ar), 96.4 (C3), 95.0 (C5), 80.1 (q Boc), 67.7 (CH2-Ph), 50.6, 50.5 (C1 1 , C12), 47.9 (C7), 46.1 (2C, C13), 43.1 (2C, C14), 35.4 (C10), 28.1 (3C, Boc), 27.7 (C8), 26.5 (C9); HRMS (ESI+): calculated for C28H37N4O5: 509.2758, found [M+H]+: 509.2733.

31166-44-6, 31166-44-6 1-Cbz-Piperazine 643495, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; THE UNIVERSITY OF BRISTOL; GALLAGHER, Timothy Charles; REGO CAMPELLO, Hugo; (154 pag.)WO2018/33742; (2018); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

In 2 mL of dimethyl acetamide were combined tert-butyl 4- chloro-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate (1.0 g, 3.7 mmol), triethylamine (1.0 mL, 7.4 mmol), and benzyl 1-piperazinecarboxylate (0.86 mL, 4.4 mmol). The reaction vessel was sealed and the reaction mixture was heated to 90 C with stirring. After 5 hours, the reaction was diluted with brine and extracted with methyl t-butyl ether. The combined organic layers were washed sequentially with saturated ammonium chloride and brine, dried over MgSC”4, and concentrated under reduced pressure to a thick oil. The oil was chromatographed (RediSep, 24 g) eluting withl : l ethyl acetate/Hexanes to give tert-butyl 4-(4- ((benzyloxy)carbonyl)piperazin-l-yl)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate (1.3 g, 2.9 mmol, 77 % yield). ES+APCI MS m/z 454.2 [M+H]+., 31166-44-6

31166-44-6 1-Cbz-Piperazine 643495, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : DIPEA (879 mu, 5.17 mmol) was added to 5-bromo-2-chloropyrimidine Ex.10a (500 mg, 2.56 mmol) in acetonitrile (12 mL). Then, benzyl piperazine-1-carboxylate (500 mu, 2.56 mmol) was added to the mixture. The reaction mixture was stirred at r.t. for 60h. Water and EtOAc were added. The two phases were separated and the aqueous solution was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography on silica gel eluting with Heptane/EtOAc from [100:0] to [0:100]. The product fractions were combined and concentrated to dryness to afford benzyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate Ex.10a (858 mg, 88percent) as white solid.

31166-44-6, The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

Cbz lnt-1 a A mixture of 5-fjiioro-2-nitrobenzaldehyde (20 g, 118 mmol) in DMF (150 mL), benzyl 1-piperazine carboxylate (31.2 g, 142 mmol), and triethylamine (14.3 g,142 mmol) was heated to 80 °C for 15 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (300 mL), washed with brine (3 x 150 mL), dried over Na2S04, filtered, and concentrated. The resulting thick oil was purified by a flash column, eiuting with 20percent EtOAc/hexanes to yield 36.2 g (86percent) of Int-la as a yellow solid., 31166-44-6

The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SCHERING CORPORATION; XIAO, Dong; PALANI, Anandan; ASLANIAN, Robert, G.; DEGRADO, Sylvia; HUANG, Xianhai; ZHOU, Wei; SOFOLARIDES, Michael; CHEN, Xiao; WO2011/75375; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of compound 7 (0.16 g, 0.37 mmol) and isonipecotic acid ethyl ester (0.086 ml, 0.56 mmol) in CH2Cl2 was added WSCI*HCl (0.11 g) and HOBt (0.085 g), and then the mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with water and the organics were extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, then concentrated in vacuo, and then the residue was purified with silica gel column chromatography (0-5percent MeOH-CH2Cl2 as eluent) to give compound 8 (0.16 g, 0.28 mmol, 76percent) as a colorless powder., 31166-44-6

The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Ichikawa, Masanori; Yokomizo, Aki; Itoh, Masao; Sugita, Kazuyuki; Usui, Hiroyuki; Shimizu, Hironari; Suzuki, Makoto; Terayama, Koji; Kanda, Akira; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1930 – 1949;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

Example 15(2)4-(4-((4-benzyloxycarbonyl)-1-piperazinecarbamoyl)piperidin-1-yl)-benzoic acid tert-butyl esterThe 4-(4-phenoxycarbonylaminopiperidin-1-yl)-benzoic acid tert-butyl ester (13.88 g, 35.0 mmol) obtained in Example 15(1) was dissolved in acetonitrile (150 ml), and N-benzyloxycarbonylpiperazine (7.71 g, 35.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (6.6 ml, 42 mmol) were added thereto under ice-cooling, followed by stirring at room temperature for 19 hours.Then, water was added thereto, and the precipitate was collected by filtration, thereby obtaining 4-(4-((4-benzyloxycarbonyl)-1-piperazinecarbamoyl)piperidin-1-yl)-benzoic acid tert-butyl ester (16.1 g, 88percent) as a milky-white solid.1H-NMR (CDCl3): delta (ppm) 1.44-1.57 (m, 11H), 2.03-2.7 (m, 2H), 2.92-3.02 (m, 2H), 3.34-3.38 (m, 4H), 3.50-3.51 (m, 4H), .78-3.92 (m,3H), 4.31 (d, J = 7.4 Hz, 1H), 5.15 (s, 2H), 6.84 (dd, J = 2.0, 7.1 Hz, 2H) ,7.31-7.38 (m, 5H), 7.85 (dd, J = 2.0, 7.1 Hz, 2H), 31166-44-6

As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

Reference：
Patent; Taiho Pharmaceutical Co., Ltd.; EP2527340; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31166-44-6,1-Cbz-Piperazine,as a common compound, the synthetic route is as follows.

To a solution of propylene oxide (4.0 mL, 57 mmol) in DCM (160 mL) was added 2.0M of trimethylaluminum in toluene (27 mL, 54 mmol) at -78 °C under N2. After being stirred at that temperature for 10 min, a solution of benzyl piperazine-l-carboxylate (from Aldrich, 9 mL, 40 mmol) in DCM (60 mL) was added. The resulting reaction mixture was stirred at -78 °C for 30 min. The reaction was then allowed to warm up to 0 °C, stirring for another 30 min. To the reaction mixture was added sodium fluoride (8.2 g, 200 mmol) in one portion, followed by water (5.2 mL, 290 mmol) slowly and periodically at 0 °C. The resulting suspension was rapidly stirred for 1 h at 0 °C and filtered through a short column of Celite and the column was subsequently washed with DCM (120 mL). The combined filtrates were dried over Na2S04, concentrated and purified on silica gel (eluting with 0-10percent MeOH in DCM) to provide the desired product (9.6 g, 76percent). LCMS calculated forCi5H23 203(M+H)+: m/z = 279.2; Found: 279.3. 3/4 NMR (500 MHz, DMSO-d6): delta 7.39-7.31 (5H, m), 8.07 (2H, s), 4.29 (1H, J= 4.0 Hz), 3.75 (1H, m), 3.38 (4H, br s), 2.38 (4H, m), 2.24 (1H, dd, J= 12.5 and 7.0 Hz), 2.17 (1H, dd, J= 12.5 and 7.0 Hz), 1.04 (3H, d, J= 6.0 Hz) ppm.

31166-44-6, As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

Reference：
Patent; INCYTE CORPORATION; RODGERS, James, D.; LI, Yun-Long; SHEPARD, Stacey; WANG, Haisheng; WO2011/28685; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics