Category: 954-81-4

Reference of 954-81-4, A common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

According to the Scott?s method4, ethyl acetoacetate (1.30 g, 10.0 mmol) was added to a solution of sodium ethoxide in EtOH, prepared from dist. EtOH (8 mL) and sodium (230 mg, 10.0 mmol). To the mixture was added N-(5-bromopentyl)phthalimide (4) (2.96 g, 10.0 mmol), and refluxed under argon for 6 hours. After cooling, the reaction mixture was neutralized with 2N HCl, and the ethanol was removed under reduced pressure. The residue was dissolved in H2O (50 mL), and extracted with Et2O (3 x 40 mL). The organic phase was combined, dried over Na2SO4, and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane : AcOEt = 2 : 1) to give 54 (2.33 g, 79%) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 1.27 (t, 3H, J = 7.3 Hz), 1.32-1.37 (m, 4H), 1.66-1.71 (m, 2H), 1.82-1.87 (m, 2H), 2.23 (s, 3H), 3.40 (t, 1H, J = 7.3 Hz), 3.67 (t, 2H, J = 7.3 Hz), 4.20 (q, 2H, J = 7.3 Hz), 7.72 (dd, 2H, J = 5.5 Hz, 3.3 Hz), 7.84 (dd, 2H, J = 5.5 Hz, 3.3 Hz). 13C NMR (75 MHz, CDCl3) delta 13.9, 26.4, 26.8, 27.8, 28.1, 28.6, 37.6, 59.6, 61.1, 123.0, 131.9, 133.7, 168.2, 169.6, 202.9. MS (FAB) 346 (M+H)+. TLC: Rf 0.40 (Hexane : AcOEt = 2 : 1).

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

Reference:
Article; Kamo, Masahiro; Tateishi, Hiroshi; Koga, Ryoko; Okamoto, Yoshinari; Otsuka, Masami; Fujita, Mikako; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 43 – 45;,
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Related Products 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.

N-(5-bromopentyl)phthalimide (1.2g, 4mmol) and thiomorpholine 1,1-dioxide (1.08g, 80mmol) and DIPEA (2ml, 11mmol) was added 10mL i-PrOH, the temperature was raised to 105 deg. C stirred for 16 hours. LCMS traced the reaction. After completion of the reaction it was concentrated, 50ml of water was added, sonicated, and filtered to give a white solid N-(5-(1,1-dioxothiomorpholin-4-yl)pentyl)phthalimide (1.0g, 97% yield).

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; Shenzen Chipscreen Biosciences Ltd.; Lu, Xianping; Liu, Jindi; Yang, Qianjiao; Li, Zhiping; Pan, Desi; Shan, Song; Zhu, Jiangfei; Wang, Xianghui; Liu, Xiangheng; Ning, Zhiqiang; (30 pag.)CN105481778; (2016); A;,
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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. Product Details of 954-81-4

General procedure: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

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

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
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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, name: N-(5-Bromopentyl)phthalimide

a) 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 h. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): delta 7.95-7.98 (m, 2H), 7.83-7.86 (m, 2H), 7.70-7.73 (m, 2H), 6.86-6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82-1.89 (m, 2H), 1.73-1.81 (m, 2H), 1.50-1.57 (m, 2H).

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; Subasinghe, Nalin; Khalil, Ehab; Ali, Farah; Hufnagel, Heather Rae; Ballentine, Shelley; Travins, Jeremy M.; Leonard, Kristi A.; Bone, Roger F.; US2005/4031; (2005); A1;,
Indoline – Wikipedia,
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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. HPLC of Formula: C13H14BrNO2

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

The synthetic route of N-(5-Bromopentyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
Indoline – Wikipedia,
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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, Recommanded Product: N-(5-Bromopentyl)phthalimide

Under a protective nitrogen atmosphere, sodium hydride (NaH, 48 mg, 1.2 mmol) is added into a solution of berbamine dihydrochloride (205 mg, 0.3 mmol) in N,N-dimethyl formamide (5 ml) at 0 C., after being stirred for 1 hour, 2-(5-bromoamyl)-isoindoline-1,3-dione (133 mg, 0.45 mmol) is added therein. The reaction solution is heated to 80 C. overnight. Then the reaction mixture is evaporated under vacuum, and purified by a preparative thin layer chromatography to give white or pale yellow compound (BS-BE-002) (98.4 mg, 39.8%). [0109] LC/MS m/z: M+1 824.2 100% (purity). 1H NMR (CDCl3) delta:7.8267.809 (dd, 2H, J=5.5 Hz, 5.5 Hz), 7.6927.680 (dd, 2H, J=6.0 Hz, 5.5 Hz), 7.267.243 (m, 2H), 7.0847.071 (d, 1H, J=6.5 Hz), 6.796.733 (m, 2H), 6.6236.607 (d, 1H, J=8.0 Hz), 6.529 (s, 1H), 6.395 (s, 1H), 6.272 (s, 1H), 5.971 (s, 1H), 4.0694.042 (t, 2H, J=6.5 Hz, 7.0 Hz), 3.783 (s, 2H), 3.750 (s, 3H), 3.7183.689 (t, 2H, J=7.0 Hz, 7.5 Hz), 3.610 (s, 1H), 3.399 (s, 1H), 3.2453.208 (m, 2H), 3.121 (s, 3H), 3.0232.779 (m, 6H), 2.569 (s, 3 H), 2.540 (s, 1H), 2.3702.338 (m, 1H), 2.250 (s, 3H), 1.9261.869 (m, 2H), 1.7884.682 (m, 3H), 1.5701.507 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; HANGZHOU BENSHENG PHARMACEUTICAL CO., LTD.; Xu, Rongzhen; Rong, Frank; Xie, Fuwen; Lai, Hongxi; US2013/158068; (2013); A1;,
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Electric Literature 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.

a 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): delta 7.95-7.98 (m, 2H), 7.83-7.86 (m, 2H), 7.70-7.73 (m, 2H), 6.86-6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82-1.89 (m, 2H), 1.73-1.81 (m, 2H), 1.50-1.57 (m, 2H).

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; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); 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. category: indolines-derivatives

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, 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; LADNER, Robert, D.; (244 pag.)WO2018/98208; (2018); A1;,
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Related Products 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.

General procedure: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

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; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: Compound 5 (5.67g, 12mmol) was added into MeCN (50mL), and then Compound 6-9 (14.2mmol) were added, respectively. After an addition of K2CO3 (5.9g, 42.6mmol), the mixture was refluxed for 24h and followed by TLC. After the solvent was removed by distillation under reduced pressure, the residue was dissolved in EtOAc (200mL), and washed by water (3¡Á50mL). The organic phase was dried by MgSO4, and then was evaporated. The crude product was purified by column chromatography (DCM/EtOAc=20:1, Rf=0.7) to give 10-13 as white solid.

The synthetic route of N-(5-Bromopentyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Duan, Xiaojiang; Ruan, Qing; Gan, Qianqian; Song, Xiaoqing; Fang, Si’an; Zhang, Xuran; Zhang, Junbo; Journal of Organometallic Chemistry; vol. 868; (2018); p. 154 – 163;,
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