Analyzing the synthesis route of (R)-2-Methylpiperazine

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

75336-86-6, (R)-2-methylpiperazine (5.025 g, 50.2 mmol) was dissolved in DCM (100 mL). A solution of boc anhydride (5.47 g, 25.1 mmol) in DCM (50 mL) was added dropwise at 0 C. The reaction mixture was stirred at rt for 1 h. The solution was filtered and concentrated under reduced pressure. Water (100 mL) was added to the residue, which was filtered again. The filtrate was saturated with K2CO3 and extracted with Et2O (3×150 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 5.04 g title compound (50%) as a solid. 1H NMR (300 MHz, CDCl3) delta ppm 1.03 (d, J=6.3 Hz, 3H) 1.45 (s, 9H) 1.56 (s, 1H) 2.30-2.46 (m, 1H) 2.65-2.72 (m, 1H) 2.74-2.76 (m, 2H) 2.93-2.95 (m, 1H) 3.93 (br s, 2H).

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2010/216812; (2010); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of 75336-86-6

75336-86-6, As the paragraph descriping shows that 75336-86-6 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.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 25 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-9-methyl-7-[(3R)-3-methylpiperazin-l- yl]pyrido[l,2-a]pyrimidin-4-one In a sealed tube, 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-7-fluoro-9-methyl- pyrido[l,2-a]pyrimidin-4-one (Intermediate 4; 50 mg, 0.155 mmol) and (R)-2-methylpiperazine (62 mg, 0.619 mmol, 4.0 eq.) were stirred in DMSO (2 mL) at 125C overnight. The solvent was removed under high vacuum. The residue was taken up in CH2CI2 and washed with an aqueous saturated solution of NaHC03. The organic layer was separated and dried over Na2S04 and concentrated in vacuo. The crude was purified by column chromatography (S1O2, CH2Cl2/MeOH=95/5 to 90/10) to afford the title product (40 mg, 70%) as a light yellow solid. MS m/z 404.3 [M+H+].

75336-86-6, As the paragraph descriping shows that 75336-86-6 is playing an increasingly important role.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PTC THERAPEUTICS INC.; RATNI, Hasane; GREEN, Luke; NARYSHKIN, Nikolai A.; WEETALL, Marla L.; (80 pag.)WO2015/173181; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about (R)-2-Methylpiperazine

75336-86-6 (R)-2-Methylpiperazine 7330434, 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.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.,75336-86-6

EXAMPLE 29; Example 29A; Step 1; (R)-2-methyl-piperazine (3.5 g, 34.9 mmol), 2-bromo-5-fluoro benzotri fluoride (7.74 g, 31.7 mmol), BlNAP (0.59 g, 0.95 mmol), tBuONa (4.58 g, 47.65 mmol) and Pd2(dba)3 (0.29 g, 0.32 mmol) were mixed in the flask and purged with N2. Anhydrous toluene (50 mL) was added and purged with N2 again. The resulting mixture was heated in an oil bath at 1000C under N2 for 3 hours. The mixture was cooled to room temperature, diluted with dichloromethane (150 mL), washed with H2O (30 mL) first, then washed with saturated brine (30 mL). The combined organic layer was dried over Na2SO4, concentrated down under reduced pressure to give a brown color liquid as crude. The crude product was purified on silica gel column eluted with 5-10percent MeOH in DCM to give (3lambda)-l-[4-fluoro-2-(trifluoromethyl)phenyl]-3-methylpiperazine as a light yellow oil (6.85 g, 82percent).; Example 29AX. 3-(((2R)-4-r4-fluoro-2-ftrifluoromethyl)phenyll-2-methylpiperazin-l – yl ) sulfonvDphenol; Step A; (R)-2-methyl-piperazine (3.88 g, 38.70 mmol), 2-bromo, 5-fluoro benzotrifluoride (8.55 g, 35.18 mmol), tris(dibenzylidineacetone)dipalldium (0) (32.0 mg g, 0.35 mmol), rac-2,2′-bis(diphenylphosphino)-l,l’-binaphthyl (657.0 mg, 1.06 mmol) and sodium tert- butoxide (5.07 g, 52.77 mmol) were charged to a reaction flask. Toluene (40 mL) was introduced under nitrogen atmosphere and the reaction mixture was heated up at 11O0C for 5.0 hours. Reaction was complete as determined by TLC. The reaction mixture was diluted with dichloromethane, washed with water, saturated brine then dried over MgSO4 and concentrated. The crude product was purified via flash column chromatography to yield (R)-I -(4-fluoro-2- (trifluoromethyl)phenyl)-3-methylpiperazine as a light brown oil (3.1 g, 33.6percent yield).

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

Reference:
Patent; WYETH; WO2007/92435; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of (R)-2-Methylpiperazine

75336-86-6, The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 5 A: A mixture of (R)-2-methyl-piperazine (6.0 g, 59.9 mmol), 4-chloro-3- trifluoromethyl-benzonitrile (11.2 g, 54.5 mmol), tris(dibenzylidineacetone)dipalldium (0) (0.499 g, 0.545 mmol), rac-2,2′-bis(diphenylphosphino)-l,l ‘-binaphthyl (1.02 g, 1.635 mmol)and sodium tert-butoxide (6.55 g, 68.12 mmol) was mixed and purged with N2. Anhydrous toluene (75 mL) was added and the resultant mixture was purged with N2 again. The resultant mixture was heated in an oil bath at 107 0C under N2 for 3 hours. After cooling, the reaction mixture was diluted with DCM (200 mL), washed with H2O (50 mL), and washed with saturated brine (50 mL). The combined organic layers were dried over Na2SO4, concentrated under reduced pressure to give a dark brown liquid. The crude product was purified using a SiO2 gel column, eluting with 5-7percent MeOH in DCM to give 4-[(3i?)-3-methylpiperazin-l-yl]-3-(trifluoromethyl)benzonitrile as a brownish red color oil (l 1.2 g, 76.2percent).

75336-86-6, The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC; WAN, Zhao-Kui; CHENAIL, Eva; IPEK, Manus; LI, Huan-Qiu; MANSOUR, Tarek, Suhayl; SURI, Vipin; XIANG, Jason, Shaoyun; SAIAH, Eddine; WO2010/141550; (2010); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of (R)-2-Methylpiperazine

As the paragraph descriping shows that 75336-86-6 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.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

75336-86-6, Intermediate 15;: (3R)-3-methyl-l-[5-(trifluoromethyl)pyridin-2-yl]piperazine; NA suspension of 2-bromo-5-trifluoromethyl-pyridine (2.37 g; 10.0 mmol; 1.0 eq.), (R)-2-methylpiperazine (2.00 g; 20.0 mmol; 2.0 eq.) and DIEA (1.94 g; 15.0 mmol; 1.5 eq.) in 4 mL of DMA was heated at 140°C for 14h. The mixture was cooled to room temperature. After evaporation of the solvent under vacuum, the residue was dissolved in a 1/1 mixture of DCM / Et2O. A 4N solution of HC1 was added (10 mL) then the resulting precipitate was collected and washed with Et2O. The solid was then poured to an aq. solution of NaOH (5N, 20 mL) and the resulting mixture was extracted with Et2O (3X). The combined organic layers were washed with brine, dried over MgSC>4, filtered and evaporated to give the title compound as an orange solid (1680 mg, 69percent) used without further purification for the next steps. M+(ESI): 246.3. HPLC (Condition A), Rt: 1.0 min (HPLC purity: 99.9 percent).

As the paragraph descriping shows that 75336-86-6 is playing an increasingly important role.

Reference:
Patent; Applied Research Systems ARS Holding N.V.; WO2006/10751; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of (R)-2-Methylpiperazine

75336-86-6, As the paragraph descriping shows that 75336-86-6 is playing an increasingly important role.

75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(3R)-3-methvM-(phenylcarbonothioyl)piperazine; A mixture of 2.8 grams (28 mmol) of (f?J-2-methylpiperaziotane and 6.0 grams (28. mmol) of S-(thiobenzoyl)thioglycolic acid was suspended in a solution of 1.6 g (40 mmol) NaOH in 50 mL of distilled water. The mixture was stirred for 5 minutes at 25 0C, and then for 5 minutes at 60 0C. The mixture was copied to 25 0C, and the ivory precipitate was collected by filtration. It was washed with distilled water, and dried in a stream of air. After further drying under high vacuum overnight there was obtained 5.1 grams of a white solid (80percent). 1HNMR (CDCI3): 7.35 – 7.20 (m, 5 H),.6.50 – 5.45 (m. 1 H), 4.80 – 4.65 (m, 1 H), 3.90 – 3.70 (m, 1 H), 3.30 – 2.70 (m, 5H)1 1.20 (d, J = 7 Hz, 1.5 H), 0.95 (d, J = 7 Hz, 1.5H).

75336-86-6, As the paragraph descriping shows that 75336-86-6 is playing an increasingly important role.

Reference:
Patent; TRIMERIS, INC.; WO2007/103456; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 75336-86-6

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

75336-86-6, i) tert-Butyl (3/?)-3-methylpiperazine-l-carboxylate;To a solution of (2No.)-2-methylpiperazine (Ig) in THF (10ml) was added di-tert-butyldicarbonate (1.45g). The reaction mixture was allowed to stir at room temperaturefor 18h.The reaction mixture was then partitioned between DCM (100 ml) and HaO (100 ml). Theorganics were separated and the aqueous layer was re-extracted with DCM (2 x 150ml).Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compoundas a clear oil. Yield: 1. Ig’H NMR: (DMSO) 8 0.92 (d, 3H), 1.38 (s, 9H), 2.57-2.70 (m, 1H), 2.76-2.81 (m, 1H), 2.87-2.99 (m, 1H), 3.66-3.74 (m, 4H)

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/24823; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about (R)-2-Methylpiperazine

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

75336-86-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 27 To a solution of Compound B (0.2 g, 0.54 mmol) in acetonitrile (5 mL) at room temperature were added diisopropylethylamine (0.4 mL, 2.3 mmol) and (R)-(-)-2-methylpiperazine (0.081 g, 0.81 mmol) and the reaction mixture was heated to 80° C. On heating, the reaction mixture became clear and after 15 min commencement of precipitation of solid was observed. Heating was continued for 3 hr and then the reaction mixture was cooled. The solid obtained was collected by filtration, washed with acetonitrile and dried under vacuum. LC/MS: (M+H)+: 435. An NMR spectrum is provided in FIG. 27.Yield: 0.13 g (55percent).

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

Reference:
Patent; Sudhakar, Anantha; US2011/105497; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of (R)-2-Methylpiperazine

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of (R)-2-methylpiperazine (7 g, 70 mmol, Aldrich) in DCM (200 mL) and DIEA (6.7 mL, 38.5 mmol, Aldrich) was added benzyl chloroformate (5 mL, 35 mmol, Aldrich) dropwise at 0 C. The mixture was then warmed up to RT and was stirred for 16 h. The solvents were removed and the residue was purified on silica gel using ISCO Combiflash system with DCM/2M methanolic ammonia gradient to give the title compound as light yellow oil. MS (ESI, positive ion) m/z: 235 (M+1)., 75336-86-6

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

Reference:
Patent; Gore, Vijay Keshav; Ma, Vu Van; Norman, Mark H.; Ognyanov, Vassil I.; Xi, Ning; US2006/84640; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 75336-86-6

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

75336-86-6,75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 26A (3R)-3-methyl-1-pyridin-2-ylpiperazine (R)-(-)-2-Methylpiperazine (0.50 g, 0.005 mol, Aldrich) and 2-bromopyridine (5 mL, 0.05 mol) were combined and heated at 120° C. for 14 hours. The reaction mixture was allowed to cool to 23° C. and partitioned between a large volume of ethyl acetate and water. The layers were separated, and then additional water was added to the ethyl acetate solution. Drops of 1 N HCl solution were added to the water/ethyl acetate mixture with vigorous mixing. The layers were separated, and the combined aqueous phases were basified to pH ~11 with a solution of saturated sodium bicarbonate and solid sodium carbonate. Sodium chloride was added, and the saturated aqueous solution was extracted with chloroform containing a few drops of isopropyl alcohol (5*). The combined organic extracts were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure to afford 0.79 g (89percent yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) delta1.02 (d, J=6.0 Hz, 3H), 2.27 (dd, J=10, 12 Hz, 1), 2.67 (m, 3H), 2.92 (m, 1H), 4.07 (m, 2H), 6.58 (dd, J=6, 8 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 7.49 (m, 1H), 8.08 (m, 1H); MS (ESI) m/e 178 (M+H)+.

75336-86-6 (R)-2-Methylpiperazine 7330434, apiperazines compound, is more and more widely used in various fields.

Reference:
Patent; Cowart, Marlon D.; Bhatia, Pramila A.; Daanen, Jerome F.; Stewart, Andrew O.; Patel, Meena V.; Kolasa, Teodozyj; Brioni, Jorge D.; Rohde, Jeffrey; US2002/169167; (2002); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics