Category: 954-81-4

Synthetic Route of 954-81-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 954-81-4, name is N-(5-Bromopentyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 3-1 (5.0 g, 17 mmol) was dissolved in dimethylformamide (DMF, 30 mL), and sodium azide (1.4 g, 1.3 eq.) was added. The reaction mixture was allowed to stir overnight, whereupon it was concentrated in vacuo to yield a white residue. The residue was dissolved in DCM, filtered through a silica gel plug, and solvent removed to afford N-[5- (azido)butyl]phthalimide (4.0 g, 91%) as a colorless thick oil. ?HNMR(300IVIHz, CDC13): = 1.30-1.44 (m, 2H), 1.50-1.75 (m, 4H), 3.21 (t, J= 7.5 Hz, 2H), 3.63 (t, J = 7.5 Hz, 2H), 7.60-7.70 (m, 2H), 7.75-7.80 (m, 2H). ?3C NIVIR(75 IVIFIz CDC13): = 23.8, 27.9, 28.2, 37.4, 51.0, 123.0, 131.9, 133.7, 168.2.

The chemical industry reduces the impact on the environment during synthesis N-(5-Bromopentyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUMIPHORE, INC.; BUTLIN, Nathaniel G.; MAGDA, Darren; XU, Jide; (114 pag.)WO2016/106241; (2016); A1;,
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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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, A new synthetic method of this compound is introduced below., name: N-(5-Bromopentyl)phthalimide

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). ?H NMR (400 MHz, CDC13): 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J 7.3 Hz, 2H), 2.85 (t, J 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

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; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LEWIS, Michael; (300 pag.)WO2018/98204; (2018); A1;,
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Synthetic Route of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

(cis) 1-(1 /-/-Benzimidazol-2-ylmethyl)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10- phenanthroline (0.045 g, 0.14 mmol), 2-(5-bromopentyl)-1 /-/-isoindole-1 ,3(2H)-dione (0.062 g, 0.21 mmol), potassium iodide (5 mg), and N,N-diisopropylethylamine (0.050 g, 0.31 mmol) in 3 mL of dimethylformamide were heated to 80 9C for 16 hours. The mixture was allowed to cool to room temperature and hydrazine (0.4 mL, 14.0 mmol) was added. The mixture stirred at room temperature overnight. The mixture was quenched with water and extracted 3 times with ethyl ether. The ether layers were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of 30% aqueous ammonium hydroxide in acetonitrile to yield 0.01O g (18%) of (cis)-5-[2-(3,4,4a,5,6,10b- hexahydro-1 ,10-phenanthrolin-1 (2/-/)-ylmethyl)-1 H-benzimidazol-1-yl]-1- pentanamine. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.0 (m, 2 H), 1.3 (m, 3 EPO H), 1.4 (s, 2 H), 1.6 (m, 1 H), 1.7 (m, 2 H)1 2.1 (m, 1 H), 2.3 (m, 2 H), 2.5 (m, 3 H), 2.8 (m, 1 H), 2.9 (m, 1 H), 3.1 (m, 1 H), 3.4 (s, 1 H), 3.5 (d, J=13.9 Hz, 1 H), 3.9 (m, 1 H), 4.1 (m, 1 H), 4.2 (d, J=13.9 Hz, 1 H), 7.2 (m, 2 H), 7.3 (m, 2 H), 7.5 (d, J=7.1 Hz, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (s, 1 H); MS m/z404 (M+1).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
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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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, A new synthetic method of this compound is introduced below., Formula: C13H14BrNO2

General procedure: A suspension of isovanillin (8 g, 52.6 mmol, 1 equiv), anhydrous K2CO3 (10.9 g, 78.9 mmol, 1.5 equiv), and KI (1.75 g, 0.1 equiv) in dry DMF (50 mL) was stirred and heated to 65C. Compounds 6a-d (68.4 mmol, 1.3 equiv) was added portionwise over 1 h and the stirred mixture heated at 65 C for a further 18 h. After cooling to room temperature, the reaction mixture was treated with 1M aqueous HCl (100 ml), and extracted with CCl3H (2 × 100 ml), The combined organic extracts were separated, dried, filtered, and concentrated. The residue was purified by flash chromatography to provide 7a-d as a white solid. Isovanillin was treated with compound 6c according to general procedure to give the desired product 7c as a white solid, yield 81%.

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:
Article; Liu, Anqiu; Huang, Ling; Wang, Zhiren; Luo, Zonghua; Mao, Fei; Shan, Wenjun; Xie, Jiaxing; Lai, Kefang; Li, Xingshu; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1548 – 1552;,
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Application of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

[0715] Step 12: Synthesis of S-(5-(1,3-dioxoisoindolin-2-yl)pentyl)ethanethioate (15-k) To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). 1H NMR (400 MHz, CDCl3): delta 7.84 (dd, J = 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J = 5.5 Hz, 3.1Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 2.85 (t, J = 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, belongs to indolines-derivatives 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 954-81-4, Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: To a suspension of compound 9-12 and potassium carbonate in ACN, was added dropwise N-methylbenzylamine or piperidine under stirring and the reaction mixture was refluxed for 24 h. The reaction mixture was cooled and filtered. After evaporation of the filtrate, purification by column chromatography on silica gel (cyclohexane/EtOAc/TEA) yielded compounds 16 and 17.

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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Reference of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

To a suspension of compound 9 (12.0 g, 40.5 mmol) and potassium carbonate (14.0 g, 101 mmol) in THF (150 mL) was added dropwise an excess of a dimethylamine aqueous solution (26% wt) (39 mL, 202.5 mmol) and the reaction mixture was refluxed for 24 h. After cooling, the solution was filtered and the precipitate was washed with THF (200 mL). After concentration under reduced pressure, the filtrate afforded a biphasic residue that was decanted. The oily layer was separated to yield a first fraction of compound 13a. The remaining aqueous layer was extracted with EtOAc (2 × 75 mL), the organic extracts were combined, dried over MgSO4, filtered and evaporated under vacuum to afford a supplementary fraction of compound 13a. The two fractions (6.95 g, 34.0 mmol) were combined and engaged directly in the next step without further purification. Yield 84%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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Electric Literature of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). (1333) 1H NMR (400 MHz, CDC13): delta 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J= 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++l).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

954-81-4, name is N-(5-Bromopentyl)phthalimide, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C13H14BrNO2

General procedure: To a stirred solution of 2-5 (5 mmol) in THF (60 mL) was added potassium thioacetate (15 mmol), and the mixture was refluxed for 3-4 h. And the solvent was evaporated to dryness in vacuo, and then added water (30 mL), and the organic materials were extracted with EtOAc (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:8) to give compounds 6-9 as white powder.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, A new synthetic method of this compound is introduced below., Product Details of 954-81-4

Step 1: Preparation of tert-Butyl 4-(5-(1,3-dioxoisoindolin-2-yl)pentyl)-2-phenylpiperazine-1-carboxylate In a microwave vial, tert-butyl 2-phenylpiperazine-1-carboxylate (500 mg, 1.906 mmol, 1 eq), cesium carbonate (1863 mg, 5.72 mmol, 3 eq), and 2-(5-bromopentyl)isoindoline-1,3-dione (564 mg, 1.906 mmol, 1 eq) were dissolved in DMF (3 mL). The reaction was put in the microwave for 25 min at 110 C. The mixture was taken up in EtOAc and water extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated, and purified by silica gel chromatography to give the title compound (460 mg, 50.5% yield) as a colorless oil.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BECKWITH, Rohan Eric John; JIANG, Hua; WANG, Ce; (54 pag.)US2018/271837; (2018); A1;,
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