109-07-9 | Page 12 of 12 | Heterocyclic Building Blocks-piperazine

Simple exploration of 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 2-chloro-5-trifluoromethylpyridine (2.34 g, 12.9 mmol, 1.0 equiv.), 2-methypiperazine (2.59 g, 25.8 mmol, 2.0 equiv.) and triethylamine (5.4 mL, 38.7 mmol, 3.0 equiv.) in toluene (20 mL) was sealed in a 50 mL of high pressure reaction tube. The reaction mixture was heated to 150 C. with stirring. After stirring at 150 C. for 20 hours, the reaction mixture was cooled to room temperature and then diluted with CH2Cl2 (200 mL). The organic mixture was washed with water (100 mL¡Á2), brine and then dried over Na2SO4. After filtration and removal of solvent, 3.05 g (96% yield) of the desired intermediate was obtained as a bright yellow solid, which was used without purification. 1H NMR (400 MHz, CDCl3), delta (ppm): 8.42 (m, 1H), 7.65 (dd, 1H), 6.66 (d, 1H), 4.26 (m, 2H), 3.14 (m, 1H), 2.94 (m, 3H), 2.60 (dd, 1H), 1. 18 (d, 3H)., 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 99 N- (2-Methoxy-5-methylphenyl)-7- [ (3-methylpiperazin-1-yl) methyl]-1-benzofuran-5- sulfonamide, trifluoroacetate A mixture of 7-formyl-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide (100 mg, 0,29 mmol; Intermediate 62), 2-methylpiperazine (32 mg, 0,32 mmol) and sodium triacetoxyborohydride (245 mg, 1,16 mmol) in 1, 2-dichloroethane (3 mL) was stirred overnight. Filtration and concentration provided 100 mg of crude material that was purified by preparative HPLC to after concentration give 30 mg (19 %) of the title product. OH NMR (400 MHz, methanol-d4) 8 1.27 (d, 3 H), 2.24 (s, 3 H), 2.33-2. 40 (m, 1 H), 2.46-2. 55 (m, 1 H), 2.91-2. 98 (m, 1 H), 3.05-3. 17 (m, 2 H), 3.32-3. 38 (m, 1 H), 3.39 (s, 3 H), 3.96- 4. 08 (m, 2 H), 6.64 (d, 1 H), 6.87 (dd, 1 H), 6.97 (d, 1 H), 7.28 (d, 1 H), 7.66 (d, 1 H), 7.91 (d, 1 H), 8. 04 (d, 1 H); MS (ESI+) for C22H27N304S m/z 430 (M+H) + ; HPLC 99 %, RT=1. 66 in (System A; 10-97% MeCN over 3 min), 99% RT=1.46 (System B; 10-97% MeCN over 3 min)., 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; BIOVITRUM AB; WO2005/58858; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Method 1 1-(t-Butoxycarbonyl)-3-methylpiperazine To a cold (-5 C.) solution of 2-methylpiperazine (5.00 g, 0.05 mole) in 200 mL of CH2 Cl2 under Ar was added a solution of di-t-butyl dicarbonate (10.9 g, 0.05 mole) in 100 mL of CH2 Cl2 over 1 h. The resulting mixture was stirred at -5 C. for 1 h and then at r.t. for 2 h. The solution was then washed (H2 O), dried (Na2 SO4) and evaporated to give an oil which was chromatographed (SiO2 /ethyl acetate then ethyl acetate-MeOH-NH4 OH 10:1:0.1) to give the product (4.30 g, 43%) as an oil. This material was used without further purification: 1 H nmr (200 MHz, CDCl3) delta4.15-3.75 (br s, 2H), 3.0-2.6 (m, 4H), 2.47-2.35 (m, 1H), 1.48 (s, 9H), 1.08 (d, J=6.7 Hz, 3H)., 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; Bristol-Myers Squibb Company; US5300506; (1994); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 109-07-9

109-07-9, As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thermometer, vacuum stirrer, four-necked flask 2L equipped with acooling tube, L- tartaric acid 270g (1.8 mol), acetic acid 108 g (1.8 mol), water 270g was added,was completely dissolved. Then, (¡À) -2- methylpiperazine 300g (3.0 mol), water 300g wasadded, and the reaction was heated 85 C or more, were completely dissolved. Then cooled to6874 C, (R) -2- methylpiperazine and L- diastereomers tartaric was added to precipitatecrystals, allowed to 1 hour aged at that temperature. Then, over a period of 5 hours and cooled to1218 C, and the precipitated crystals were filtered, diastereomeric salt 440g of wet biomass,liquid content 22.7wt%, optical purity of 92.3% e. e. , R KaradaOsamuritsu Retrieving salt to theR-isomer of charge (¡À) in the 2-methyl piperazine, was 88%. Then, charged 644g of water four-necked flask 2L, the resulting crystals 440g ((R) -2-methylpiperazine pure content = 132 g) were added. Furthermore, the addition of calciumhydroxide 162g (2.2mol), then heated to 80 C, and aged at that temperature for 5 hours.Cooled over a period of 2 hours up to 25 C, was filtered off precipitated crystals to remove thewet material crystal of 586g (mainly L- tartaric acid calcium). Get the filtrate 660 g, liberated with L- tartaric acid in the filtrate (R) -2- methylpiperazine were present 130 g. Thermometer, vacuum stirrer, four-necked flask 1L with a cooling tube equippedfiltrate 330g obtained in Reference Example 1 (in the filtrate of (R)-2-methyl-piperazine 65 g)was concentrated under reduced pressure, (R ) concentration of 2-methyl piperazine was distilledoff the water until the 30 percent. Then, toluene 356g was added to the concentrate, a mixedsolution was heated under normal pressure and azeotroped with water and toluene in arms 84 to87 C, excluding the water. Then, toluene was distilled off 212g under reduced pressure. Theconcentrate was cooled to 47 C, (R) -2- methylpiperazine 0.01g was added as a seed crystal toprecipitate crystals, followed by aging for 1 hour at 47 C. Was cooled over 5 hours 05 C,and aged for 2 hours at 06 C. The precipitated crystals were taken out by filtration underreduced pressure, vacuum drying, the crystalline body (R) -2- methylpiperazine was 45gacquired. The resulting quality of (R) -2- methylpiperazine of the crystal body, chemical purity of100%, an optical purity of 99.5% e. e. In and, R KaradaOsamuritsu acquisition crystals for (R) -2-methylpiperazine in charge filtrate was 69%. 1, illustrating the steps from Reference Example 1 to Example 1. Was the first crystallizationfrom ( “1 crystallization” was described as) (described as “crystallization”) last crystallization upto six steps. Compared to the Comparative Example 2 step, short process, was able to get a goodoptically active 2-methylpiperazine of easy nature of handling. Thermometer, vacuum stirrer, four-necked flask 1L with a cooling tube equippedfiltrate 330g obtained in Reference Example 1 (in the filtrate of (R)-2-methyl-piperazine 65 g)was concentrated under reduced pressure, (R ) concentration of 2-methyl piperazine was distilledoff the water until the 30 percent. Then, cyclopentyl methyl ether 356g added to theconcentrated solution, mixed solution was heated to normal pressure and azeotroped water andcyclopentyl methyl ether at 8487 C, except for the water. It was then distilled off cyclopentylmethyl ether 205g under reduced pressure. The concentrate was cooled to 47 C, (R) -2-methylpiperazine 0.01g was added as a seed crystal to precipitate crystals, followed by aging for1 hour at 47 C. Was cooled over 5 hours 05 C, and aged for 2 hours at 06 C. Theprecipitated crystals were taken out by filtration under reduced pressure, vacuum drying, thecrystalline body (R) -2- methylpiperazine was 44g acquired. The resulting quality of (R) -2-methylpiperazine of the crystal body, chemical purity of 100%, an optical purity of 99.6% e. e. Inand, R KaradaOsamuritsu acquisition crystals for (R) -2- methylpiperazine in charge filtrate was 68%. Thermometer, vacuum stirrer, four-necked flask 1L equipped with a Dean-Starkapparatus, 33% (S) -2- methylpiperazine solution 300.0g ((S) -2- methylpiperazine 100.0 g,Quality: Chemistry purity 99.9%, optical purity of 80.0% e.e. ) Were charged. Then stirred withtoluene 586.0g (5.86wt times / (S) -2- methylpiperazine). The solution was heated under normalpressure, arms 84 to 87 was azeotroped with water and toluene in C, except for water only.Then, toluene was distilled off 286g under reduced pressure. The concentrate was cooled to4350 C, (S) -2-methylpiperazine 0.01g was added as a seed crystal to precipitate crystals,followed by aging for 1 hour at 4350 C. Then it cooled over 2 hours to 0 to 5 C, and agedfor 2 hours at 05 C. The precipitated crystals were taken out by filtration under reducedpressure, vacuum drying, the crystalline body (S)-2-methylpiperazine 66.8g was obtained (67%yield). The resulting quality of the crystal of (S) -2- methyl piperazine, the chemical p…

109-07-9, As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; TORAY FINE CHEMICALS COMPANY LIMITED; MORII, SEIJI; NISHIKAWA, TAKESHI; (12 pag.)JP2016/37495; (2016); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Some tips on 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference Example 10 benzyl 3-methylpiperazine-1-carboxylate A 4 g portion of 2-methylpiperazine was dissolved in 40 ml of dichloromethane, and 1.71 g of benzyl chloroformate was added dropwise thereto at -78 C. After 1 hour of stirring, the mixture was washed by adding water and dried and then the solvent was evaporated to obtain 2.0 g of the title compound., 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yamanouchi Pharmaceutical Co. Ltd.; US6673799; (2004); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Some tips on 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various.

Method 1 1-(t-Butoxycarbonyl)-3-methylpiperazine To a cold (-5¡ã C.) solution of 2-methylpiperazine (5.00 g, 0.05 mole) in 200 mL of CH2 Cl2 under Ar was added a solution of di-t-butyl dicarbonate (10.9 g, 0.05 mole) in 100 mL of CH2 Cl2 over 1 h. The resulting mixture was stirred at -5¡ã C. for 1 h and then at r.t. for 2 h. The solution was then washed (H2 O), dried (Na2 SO4) and evaporated to give an oil which was chromatographed (SiO2 /ethyl acetate then ethyl acetate-MeOH-NH4 OH 10:1:0.1) to give the product (4.30 g, 43percent) as an oil. This material was used without further purification: 1 H nmr (200 MHz, CDCl3) delta4.15-3.75 (br s, 2H), 3.0-2.6 (m, 4H), 2.47-2.35 (m, 1H), 1.48 (s, 9H), 1.08 (d, J=6.7 Hz, 3H)., 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various.

Reference£º
Patent; Bristol-Myers Squibb Company; US5300506; (1994); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of 109-07-9

109-07-9, The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

A. To a solution of 2-methylpiperazine (0.10 g, 1 mmol) in CH2Cl2 (2 mL) was added 4-fluorobenzyl bromide (0.125 mL, 1 mmol). The resultant mixture was stirred at ambient temperature. After 15 hours, the mixture was concentrated in vacuo to afford a solid. This solid was dissolved in CH2Cl2 and washed sequentially with water, aqueous NaHCO3 solution, then brine. The organic layer was dried over MgSO4, filtered, and concentrated to an oil. Purification by flash column chromatography afforded 0.025 g (12% yield) of 1-(4-fluorobenzyl)-3-methylpiperazine, a compound of formula (C), as a colorless oil; NMR (CDCl3) 7.3 (m, 2), 7.0 (m, 2), 3.4 (s,2), 3.0-2.6 (m, 5), 2.0 (br s, 2), 1.6 (t, 1), 1.0 (d, 3) ppm.

109-07-9, The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Aktiengesellschaft; US6207665; (2001); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 29 2-(4-Chlorophenoxy)ethyl 3-(3-methyl-1-piperazinyl)-2-pyrazinyl Ether The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(4-chlorophenoxy)ethoxy]pyrazine* (150 mg, 0.53 mmol) and 2-methylpiperazine (256 mg, 2.56 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This gave 143 mg (77%) of the title product. HRMS m/z calcd for C17H21ClN4O2 (M)+348.1353, found 348.1370. Anal. (C17H21ClN4O2) C, H, N. *Prepared according to the procedure described in Example 4, Step 1., 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Biovitrum AB; US6465467; (2002); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

To a solution of 5-bromobenzofuran (250 mg, 1.27 mmol, 1.0 equiv.) and 2-methylpiperazine (508.4 mg, 5.08 mmol, 4.0 equiv.) in toluene (7 mL) was added PdCl2[P(o-Tol)3]2 (30 mg, 0.04 mmol, 0.04 equiv.) followed by sodium tert-butoxide (183 mg, 1.91 mmol, 1.5 equiv.). The resulting mixture was heated to 100 C. with stirring under nitrogen. After stirred at same temperature for 16 hours, the reaction mixture was cooled to room temperature and then diluted with ethyl acetate (100 mL). The resulting solution was washed with water, brine and then dried over Na2SO4. After removal of solvent, the crude product was purified by chromatography to give 132 mg (48% yield) of 1-Benzofuran-5-yl-3-methyl-piperazine. 1H NMR (400 MHz, CDCl3), delta (ppm): 7.56 (d, 1H), 7.39(d, 1H), 7.10 (d, 1H), 7.00 (dd, 1H), 6.69 (m, 1H), 3.44 (d, 2H), 306 (m, 3H), 2.72 (dt, 1H), 2.38 (d, 1H), 1.14 (d, 3H).

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various.

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 11 An experiment was carried out as described for Example 9, except that 45.55 g of 1-butanol and 4.61 g of water (water content 9.2 wt%) were used instead of 50.00 g of 1-butanol. As a result, the conversion of 2-methylpiperazine was 94.3%, and the selectivity of 1-tert-butoxycarbonyl-3-methylpiperazine was 85.8% (reaction yield 80.9%).Comparative Example 8 An experiment was carried out as described for Example 9, except that 37.56 g of 1-butanol and 12.67 g of water (water content 25.2 wt%) were used instead of 50.00 g of 1-butanol. As a result, the conversion of 2-methylpiperazine was 81.6%, and the selectivity of 1-tert-butoxycarbonyl-3-methylpiperazine was 70.9% (reaction yield 57.9%).Comparative Example 9 An experiment was carried out as described for Example 9, except that 25.00 g of 1-butanol and 25.00 g of water (water content 50.0 wt%) were used instead of 50.00 g of 1-butanol. As a result, the conversion of 2-methylpiperazine was 81.2%, and the selectivity of 1-tert-butoxycarbonyl-3-methylpiperazine was 41.8% (reaction yield 33.9%).

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various.

Reference£º
Patent; Toray Fine Chemicals Co., Ltd.; EP1548010; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics