Category: 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. Formula: C13H14BrNO2

4.1.7 Synthesis of 5-N-phthalimido-1-pentyl 2′,2′,2′-trifluoroethyl sulfide 13 ( Scheme 3 ) To a solution of sodium methoxide, prepared by dissolving sodium (1.1 g, 47.82 mmol) in methanol (80 mL), a 2,2,2-trifluoroethanethiol (5 g, 43.0626 mmol) was added and left at room temperature for 1.5 h. N-(5-bromopentyl)phthalimide was added and the mixture was stirred at room temperature for 48 h. After removal of methanol the residue was dissolved in chloroform and the solution was washed with water. The organic layer was dried with MgSO4 and the solvent was removed under vacuum. The crude product was purified by column chromatography (silica gel, dichloromethane as solvent) to give pure sulfide 13 as a solid, mp = 89 C (13.88 g, 98%). 1H NMR (CDCl3): delta 1.41-1.50 (m, 2H), 1.58-1.77 (m, 4H), 2.65 (t, 2H, J = 7.20 Hz, CH2S), 3.05 (q, 2H, JH-F = 10.03 Hz, CH2CF3), 3.69 (t, 2H, J = 7.07 Hz, CH2N), 7.67-7.82 (m, 4H, arom). 19F NMR (CDCl3): delta – 65.8 (t, 3F, JH-F = 10.30 Hz). 13C NMR (CDCl3): delta 25.79, 28.11, 28.56, 32.99, 34.31 (q, JC-F = 32.31 Hz, CH2CF3), 37.69, 123.24, 125.97 (q, JC-F = 125.97 Hz, CF3CH2), 132.11, 133.97, 168.47. MS (CI, isobutane): m/z = 332.1 [M + H]+. HRMS: m/z calcd for [M + H]+ C15H17F3NO4S 332.09321, found 332.09272.

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

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., Formula: C13H14BrNO2

General procedure: 4.2.1 Synthesis of ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate (3a). To a solution of 2 (0.20 g, 0.99 mmol) in anhydrous DMF (3 mL) under N2 at 0 C was added NaH (0.044 g, 1.09 mmol). The mixture was warmed to rt and stirred for 30 min. After cooling back to 0 C, ethyl bromoacetate (0.12 mL, 1.09 mmol) was added and the mixture stirred at rt for 2 h. The reaction was quenched with saturated NH4Cl (10 mL) and the product extracted into ethyl acetate (3*30 mL). The combined organic extract was dried (Na2SO4) and the solvent removed in vacuo. Excess DMF was removed by Kugelrohr distillation. The crude product was purified by radial chromatography (hexane/ethyl acetate gradient) to give ester 3a (0.26 g, 93%) as a white solid.

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Application 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.

[69] Potassium carbonate (13.57 g, 98.20 mmol), pyrrolidine (4.47 ml, 54.01 mmol) and sodium iodide (7.359 g, 49.098 mmol) were added to ethanol/acetone (1:1) at room temperature and stirred for 1 hour. To the reaction mixture was slowly added N – (5-bromopentyl)phthalimide (2) (10.60 g, 49.10 mmol), and the resulting reaction mixture was refluxed at 50 0C for 24 hours. After the reaction was completed, the resulting white solid was filtered and the solvent was evaporated under reduced pressure. Afterwards, the obtained residue was extracted with a saturated IN NaOH aqueous solution and dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane :methnol: ammonia water = 100:9:1) to give the target compound (3.27 g, 45 %).[70] 1H-NMR (400 MHz, CDCl3) delta 7.81-7.66 (m, 4H, aromatic), 3.66-3.63 (t, 2H, -CH2 -(CH2)4-NC4H8), 2.51-2.49 (t, 4H, -(CH2)S-NC2H4C2H4), 2.45-2.41 (m, 4H, -(CH2)5-NC2 H4C2H4), 1.77-1.74 (m, 2H, -(CH2VCH2-NC4H8), 1.68-1.55 (m, 4H, -CH2-CU2-CU2 – CH2-CH2-NC4H8), 1.36-1.32 (m, 2H, -CH2-CH2-CH2 -CH2-CH2-NC4H8).

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

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.

General procedure: To a suspension of compound 9-12 (20 mmol) and potassium carbonate (50 mmol) in ACN (150 mL) was added dropwise the secondary amine (4 eq.) and the reaction mixture was refluxed for 24 h. After cooling, the reaction mixture was filtered and the filtrate was concentrated to afford an oil that was directly engaged in the next step without further purification. Reactions were performed on a scale of 5 to 20 g of compounds 9-12 to afford amines 14 and 15 with the following yields: 14a, Yield 90%; 14b, Yield 93%; 15a, Yield 89%; 15b, quantitative yield; 15c, Yield 35%.

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.

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

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.

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:
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;,
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Reference 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 mm at room temperature .Afier 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 I h. The resultant precipitate was filtered, washed with water (500 rnL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%).?H NMR (40() MHz, C1)Ci3): d 7.84 (dd, J= 5.5 Hz, 3.() Hz, 2K), 7.71 (dd, j:zr. 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, 1Ff), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

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; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); A1;,
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Indoline | C8H9N – PubChem

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.

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into 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; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
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Reference of 954-81-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 954-81-4, name is N-(5-Bromopentyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of N-(5-bromopentyl)phthalimide (5 g, 16.9 mmol) in ACN (50 mL) was added N-benzylmethylamine (2.04 g, 16.9 mmol), followed by DIPEA (2.93 mL, 16.9 mmol). The reaction mixture was stirred at 50 C. for 3 hours and then the solvent was removed in vacuo. The residue was dissolved in DCM (100 mL), washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in MeOH (100 mL) and hydrogenated to remove the benzyl group using palladium on activated carbon (1 g, 10 wt. % (dry basis)) as a catalyst under a hydrogen gas balloon at room temperature overnight. The mixture was filtered through Celite and the solvent was removed in vacuo to yield 4.2 g of the title intermediate as a solid.

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:
Patent; Theravance, Inc.; US2005/203083; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Safety of N-(5-Bromopentyl)phthalimide

60 g (0.302 mol) N-[(E)-4-pyridylmethyleneamino]aniline in 350 ml N,N-dimethyl5 formamide were stirred at 20C under argon atmosphere. The reaction mixture wascooled down -30C. 22 g (0.903 mol) sodium hydride was added slowly while keeping the reaction temperature below -25C. Afterwards, a solution of 121 g (0.452 mol) N-(5-bromopentyl)phthalimide in 500 ml N,N-dimethylformamide was added into the mixturedropwise within one hour. After the addition, the product mixture was warmed to 20Cand continued to stir for another 12 hours. Then, the reaction was quenched by adding20 ml water. Another 600 ml water were poured into the reaction mixture. The formedprecipitate was collected by filtration and washed with distilled water. The obtainedcrude product was used for the next step directly without further purification.Yield: 88 g (75%), yellow solid.ESI-MS m/z 412.2 [W].

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:
Patent; BASF SE; BACHMANN, Frank; CREMER, Christian; FROEHLING, Beate; MURPHY, Bryan Patrick; ZHANG, Guiru; TORGERSON, Peter Marte; (123 pag.)WO2016/146813; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 mixture of N-(5-bromopentyl)phthalimide (1.49 g, 5 mmol) and N,N-diisopropylethylamine (870 muL, 5 mmol) was dissolved in NMP (2 mL) followed by morpholine (870 muL, 5.5 mmol). The reaction mixture was stirred at room temperature overnight, the formed precipitate was filtered, and the filtrate evaporated. The crude product was triturated from EtOAc, filtered, and dried in vacuo to provide the alkylated morpholine intermediate (939 mg) as a white solid. The intermediate was dissolved in ethanol (20 mL) then treated with hydrazine hydrate (155 muL, 3.1 mmol). The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the formed precipitate was filtered. The filtrate was concentrated in vacuo, and the resulting residue was dissolved in chloroform (5 mL) followed by treatment with N-(9-fluorenylmethoxycarbonyl)-isothiocyanate (872 mg, 3.1 mmol) The reaction mixture was maintained at room temperature for 2 h, then concentrated in vacuo. The resulting oil was dissolved in EtOAc (5 mL), treated with piperidine (614 muL, 6.2 mmol), stirred at room temperature for 30 min, and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (10 mL), and the formed precipitate was filtered and dried in vacuo to provide 1-(5-morpholinopentyl)thiourea (287 mg, 58%) as a yellowish amorphous solid.

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

Reference:
Patent; Dickson, John K.; Hodge, Carl Nicholas; Mendoza, Jose Serafin; Chen, Ke; US2006/52416; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem