Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1758-46-9, HPLC of Formula: C8H11NO

Example 55; 6- (2-Phenoxy-ethylamino)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine Hydrochloride; Use a method similar to the General Procedure 5-1, using 3- (2, 2,2-trifluoroacetyl)- 6-trifluoromethanesulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [dlazepine (100 mg, 0.23 mmol) and phenoxyethylamine (63 mg, 0.4 mmol) to give, after chromatography on silica gel eluting with hexane/EtOAc (85: 15) followed by SCX chromatography, 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-1H-benzo[d]azepine as a yellow oil. MS (ES+) m/z : 379 (M+H) +. Use a method similar to the General Procedure 1-1 to deprotect 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (75 mg, 0.19 mmol). Purify by SCX chromatography to give the free base of the title compound. Use a method similar to the General Procedure 2-2 to give the title compound as a white solid. MS (ES+) m/z : 283 (M+H) +.; General Procedure 5-1; Dissolve the appropriately substituted 3- (2, 2, 2-trifluoroacetyl)-6-trifluoromethane- sulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (1 equiv. ), palladium (II) acetate (0.1- 0.4 equiv. ), BINAP (0.2-0. 8 equiv. ; BINAP/catalyst ratio 2: 1) and cesium carbonate (1.4- 3. 0 equiv. ) in toluene (0.2-0. 05 M solution). Add the amine (1-3 equiv. ), degas the mixture with vacuum/nitrogen or argon purge and heat at 80-110°C for 4-16 h. Cool the mixture to ambient temperature, dilute with EtOAc, filter through a pad of silica gel or through Celitet) washing with EtOAc or ether, and evaporate the solvent to obtain the crude mixture. Alternatively, partition the reaction mixture between brine or saturated aqueous NaHCO3 and EtOAc, ether or DCM, dry the organic layer over Na2S04, and concentrate to obtain the crude mixture. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc mixtures and further SCX chromatography if needed.

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Reference:
Patent; ELI LILLY AND COMPANY; WO2005/82859; (2005); A1;,
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Related Products of 1758-46-9, The chemical industry reduces the impact on the environment during synthesis 1758-46-9, name is 2-Phenoxyethylamine, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of (0.137 g, 1 mmol)-2-phenoxy ethylamine-(1.0 mmol) triethylamine-and catalyst amount of DMAP was dissolved in 20 mL dichloromethane, then (R)-2-{4-[(3-chloro-5-trifluoromethylpyridin-2-yl)oxy]phenoxy}propanoic acyl chloride was added dropwise and stirred for 1 h at room temperature. When the reaction was complete, the mixture was washed with water and brine, dried over anhydrous sodium sulfate, and vacuumed to distillate solvent. Moreover, the crude product was purified with column chromatography silica gel using PE and EtOAc as eluent to give white solid 3a-m.p. 138~140C, yield 80.1% [alpha]20 D +20.33 (c 1, CH2Cl2); 1 H NMR (400 MHz, CDCl3) delta-7.85 (d, J = 2.2 Hz, 1H, pyridine), 7.50 (dd, J1 = 9.0, J2 = 2.2 Hz, 1H, pyridine), 7.29 (s, 1H, C6H5), 7.25 (s, 1H, C6H5), 7.04 (d, J = 9.0 Hz, 2H, C6H4), 6.94 (t, J = 9.0 Hz, 3H, C6H5), 6.84 (d, J = 8.7 Hz, 2H, C6H4), 4.67 (q, J = 6.8 Hz, 1H, CHCH3), 3.97~4.10 (m, 2H, COOCH2), 3.70 (m, 2H, OCH2), 1.58 (d, J = 6.8 Hz, 3H, CH3). EI-MS m/z 480.1 [M + ]. Analysis calculated for C21H21ClFN3O3S C 64.78, H 4.78, N 9.06; found C 64.76, H 4.70, N 9.03.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Phenoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hui, Yang Zi; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 385 – 387;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1758-46-9, name is 2-Phenoxyethylamine, A new synthetic method of this compound is introduced below., Product Details of 1758-46-9

An oven-dried vial was subsequently charged with 0.1 eq. of a palladium source [Pd], 0.2 eq. (biph)P(Eu)2, 1.0 eq. 1 -(3-chloro-4-nitro-phenyl)-4-methyl-piperazine and 1.4 eq. base. The vial was evacuated and purged with argon, and the respective amine HNR1R2 (1.3 eq.) was added. The solvent was added to obtain a concentration of 1.0 M of the arylhalide 1-(3-chloro-4-nitro-phenyl)-4-methyl-piperazine. The vial was sealed and heated to 1100C for 22 h.The reaction mixture was transferred into a flask using H2O and MeOH and the total volume was reduced to less than 10 mL Purification was achieved by prep. HPLC. In order to remove any ammonium formate derivative formed during preparative HPLC, the resulting product was taken up in chloroform, extracted twice with saturated aq. NaHCO3, the combined aq. phases were re-extracted with chloroform, and the combined organic phases were dried over MgSO4.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; WO2006/69807; (2006); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 39021-83-5 as follows. Recommanded Product: 39021-83-5

A solution of 1,4-dimethoxy-2,3-dimethylbenzene 1 (1.00 g, 6.02 mmol) and N-bromosuccinimide (2.36 g, 13.2 mmol) in 1,1,1-trichloroethane (20 cm3) was heated under reflux for 1 h with visible irradiation. The mixture was filtered and the filtrate evaporated to leave the product 4 as a brown crystalline solid (0.55 g, 55%)

According to the analysis of related databases, 39021-83-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aitken, R. Alan; Jethwa, Siddharth J.; Richardson, Neville V.; Slawin, Alexandra M.Z.; Tetrahedron Letters; vol. 57; 14; (2016); p. 1563 – 1566;,
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Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1535-75-7, HPLC of Formula: C7H6F3NO

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

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Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C8H11NO

General procedure: A 10mL microwave vial was charged with 4 or 5 or 6 (1.0 mmol), a small excess (1.2 mmol) of 2-phenoxy- or (2-methoxyphenoxy)-or (2,6-dimethoxyphenoxy)-ethanamine and a catalytic amount ofpotassium iodide in 1 mL of 2-methoxyethanol. The reaction wasstirred under microwave irradiation at 160 °C (pressure 100 PSI, power 50 W) for 30 min. Then the solvent was evaporated under reduced pressure. The residue was taken up with EtOAc, basified with 5percent NaOH. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography.

The synthetic route of 2-Phenoxyethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Franchini, Silvia; Manasieva, Leda Ivanova; Sorbi, Claudia; Battisti, Umberto M.; Fossa, Paola; Cichero, Elena; Denora, Nunzio; Iacobazzi, Rosa Maria; Cilia, Antonio; Pirona, Lorenza; Ronsisvalle, Simone; Arico, Giuseppina; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 435 – 452;,
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Synthetic Route of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of 2-(((3- Methoxybenzyl)(methyl)amino)methyl)quinazolin-4(3H)-one (C). To a solution of 718 mg (3.69 mmol) of 2-(chloromethyl)-4(3H)-quinazolinone (A) in 6 mL of DMF was added 1.3 mL (1.34 g, 8.86 mmol) of 1-(3-methoxyphenyl)-N- methylmethanamine (B). The resulting solution was stirred at 120oC for 2 hours under microwave irradiation. After cooling to room temperature, the mixture was poured into 100 mL of water. The aqueous mixture stood for 5 minutes and then was extracted three times with 75-mL portions of ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was dissolved in minimal amount of ethyl acetate and precipitated by adding drops of hexanes to afford 629 mg (55%) of C as a light orange solid: 1H NMR (400 MHz, DMSO-d6) delta 11.95 (s, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.80 (td, J = 7.4, 1.2 Hz, 1H), 7.65 (d, J = 8.4 Hz, 1H), 7.50 (t, J = 7.6 Hz, 1H), 7.23 (t, J = 8.0 Hz, 1H), 7.01 (s, 1H), 6.95 (d, J = 7.6 Hz, 1H), 6.81 (dd, J = 8.0, 2.4 Hz, 1H), 3.75 (s, 3H), 3.61 (s, 2H), 3.56 (s, 2H), 2.19 (s, 3H); 13C NMR (100.5 MHz, DMSO-d6) delta 161.6, 159.2, 154.7, 148.4, 139.9, 134.3, 129.1, 127.0, 126.4, 125.8, 121.3, 121.1, 114.5, 112.5, 60.8, 59.8, 54.9, 41.5; ESI-HRMS m/z: [M+H]+ calcd for C18H19N3O2310.1550, found 310.1462.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Patent; UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.; CLARK, Geoffrey J.; TRENT, John O.; BURLISON, Joseph A.; (112 pag.)WO2017/19537; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 150-78-7, name is 1,4-Dimethoxybenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 150-78-7, HPLC of Formula: C8H10O2

In a 250 ml reaction flask, 20.0 g (0.145 mol, 1.0 eq) of hydroquinone dimethyl ether and 55 ml of glacial acetic acid were added and dissolved by ultrasonic; A solution of 15 ml of Br2 (0.290 mol, 2.0 eq) and 15 ml of glacial acetic acid was added dropwise at room temperature. After 1.5 hours, the mixture was stirred at room temperature for 2.5 h. Placed in the upper refrigerator to 10 below the temperature (not to acetic acid curing) filter; and petroleum ether washing filter cake to give a white solid, vacuum drying and then weight 35.6g, the yield of 83.6%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Huanghe Science & Technology College; Kang, Hongwei; Li, Yanchun; Ji, Mingming; (8 pag.)CN106397468; (2017); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 150-78-7, name is 1,4-Dimethoxybenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Example 2: Preparation of 2,5-dibromo-1 ,4-dimethoxybenzene (2); [00103] In a one liter round-bottom flask, a solution of bromine (35.2 g, 220 mmol) in chloroform (50 ml) was added dropwise to a solution of 1 ,4- dimethoxybenzene (13.8 g, 100 mmol) in chloroform (400 ml) under 00C. After stirring for 3 hours, 100 ml of saturated Na2CO3 solution was added. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the residue was performed recrystallization from ethanol to afford pure 2,5-dibromo-1 ,4- dimethoxybenzene (25.8 g, 85%). 1HNMR (CDCI3) 57.128 (s, 2 H), 3.873 (s, 6 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
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These common heterocyclic compound, 50742-37-5, name is (3-Phenoxyphenyl)methanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C13H13NO

EXAMPLE 5 The procedure is carried out as described in Example 1(b) but with the use of 50 g (0.25 mol) of 3-phenoxybenzylamine and 25 g (0.255 mol) of cyclohexanone. Distillation leaves 41 g (0.147 mol) of N-cyclohexylidene(3-phenoxybenzylamine), corresponding to a yield of 58.7% of theory; b.p. 135-136 C./4 Pa. Analysis for C19 H21 NO (molecular weight 279.38): calculated: C 81.69% H 7.58% N 5.01% O 5.73% found: C 80.81% H 7.56% N 5.02% O 6.12%. NMR spectrum tau [ppm]: 2.6-3.2(m), 5.51(s), 7.65(m), 8.33(m) in the ratio of 9:2:4:6.

The synthetic route of (3-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4231962; (1980); A;,
Ether – Wikipedia,
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