Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10338-57-5,4-(Piperidin-1-yl)benzaldehyde,as a common compound, the synthetic route is as follows.

Route 2: 1.94g of 4-methoxy-2-methylquinoline and 1.89g of 4-(piperidin-1-yl)benzaldehyde were added to a 250ml round bottom flask with a spherical condenser.The mixture was heated in an oil bath on an Ika magnetic stirrer, and 1.88 g of p-toluenesulfonamide was added as a catalyst, and 8 ml of toluene was used as a solvent, and the mixture was heated under reflux for 72 hours.The solvent was sparged and recrystallized from 2 ml of ethanol to give a pale yellow solid.The yield was 94%.

10338-57-5, 10338-57-5 4-(Piperidin-1-yl)benzaldehyde 291354, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; University of Science and Technology of China; Zhang Guoqing; Chen Biao; Xu Cheng; Huang Wenhuan; Huang Linkun; Bi Guoqiang; (29 pag.)CN110066243; (2019); A;,
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10338-57-5, 4-(Piperidin-1-yl)benzaldehyde is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of compound 1114 (0.34628, 111111110) and 4-piperidin-1-yl-benzaldehyde (0.20818,1.11111111)Wall pressure bottle, then add 2mL of DMS0, 10mL of trimethylchlorosilane, 100 C heating overnight, TLC monitoring reaction after the end,The crude product was purified by silica gel column chromatography (eluent: V (ethyl acetate): V (methanol): V (ammonia) = 10: 1: 0.1)To 0.4090 g of a pale yellow solid in 79% yield., 10338-57-5

10338-57-5 4-(Piperidin-1-yl)benzaldehyde 291354, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Sun Yat-Sen University; HUANG, ZHISHU; TAN, JIAHENG; WANG, YUQING; (41 pag.)CN106220631; (2016); A;,
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Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.768-66-1,2,2,6,6-Tetramethylpiperidine,as a common compound, the synthetic route is as follows.,768-66-1

A dry and nitrogen-flushed Schlenk flask equipped with a magnetic stirring bar and rubber septum was charged with iPrMgCl·LiCl (1.0 M in THF, 20 mL 20 mmol). Then, 2,2,6,6-tetramethylpiperidine (3.52 mL, 21 mmol) was added dropwise through a syringe within 5 min. The mixture was stirred until the gas evolution ceased (24-48 h). Titration against benzoic acid in THF (0 C) in the presence of 4-(phenylazo)diphenylamine as the indicator showed that the base concentration ranged from 0.9 to 0.98 M.

The synthetic route of 768-66-1 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Bozzini, Leandro A.; Batista, Joao H.C.; de Mello, Murilo B.M.; Vessecchi, Ricardo; Clososki, Giuliano C.; Tetrahedron Letters; vol. 58; 44; (2017); p. 4186 – 4190;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.72551-53-2,Ethyl 1-benzylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.,72551-53-2

A mixture of ethyl 1-benzylpiperidine-3-carboxylate (9) (5.1 g,20.62 mmol, 1 eq.) and hydrazine monohydrate (10 mL, 10 eq.) inethanol (10 mL) was stirred overnight under reflux. After cooling,the solvent and excess of hydrazine were removed under reducedpressure to afford compound 10 as colorless oil in yield of 99%; 1HNMR (400 MHz, CDCl3) delta 9.00 (s br, 1H, NH), 7.32e7.17 (m, 5H, Ar-H), 3.79 (s br, 2H, NH2), 3.47 (d, J 12.4 Hz, 1H, CHa-Ph), 3.38 (d,J 12.4 Hz, 1H, CHb-Ph), 2.62 (m, 2H, piperidin-H), 2.45 (m, 1H,piperidin-H), 2.23 (m, 2H, piperidin-H), 1.87 (m, 1H, piperidin-H),1.72-1.48 (m, 3H, piperidin-H); 13C NMR (100 MHz, CDCl3)delta 175.4, 137.3, 129.2, 128.4, 127.4, 63.4, 54.4, 53.7, 40.8, 26.7, 22.7;HRESI-MS m/z calcd. for [M+H]+ C13H20N3O: 234.1601, found:234.1604.

The synthetic route of 72551-53-2 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Abdelrahman, Mostafa H.; Youssif, Bahaa G.M.; abdelgawad, Mohamed A.; Abdelazeem, Ahmed H.; Ibrahim, Hussein M.; Moustafa, Abd El Ghany A.; Treamblu, Laurent; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 972 – 985;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4629-78-1,3-Methylpiperidin-4-one hydrochloride,as a common compound, the synthetic route is as follows.,4629-78-1

Preparation of 1-[1-(4,4′-difluorodiphenylmethoxy)-propyl]-3-methylpiperidine-4-one Compound VI: {R1 and R2 =4-F, m=1, A=(CH2)n, n=3, R4, R5 and R6 =H, R3 =CH3 } The mixture of 1-[4,4′-difluorodiphenylmethoxy]-3-chloropropane (12 g, 0.04M), 3-methylpiperidine-4-one hydrochloride (6.05 g, 0.04M), potassium carbonate (14 g, 0.10M), sodium iodide (1 g, 0.006M) and acetonitrile (200 ml) is brought to reflux for 24 hours. After cooling and filtering, the solvent is evaporated and the residue is taken up in water and CH2 Cl2; the organic phase is dried, concentrated and chromatographed on Silica (eluent: AcOEt/Cyclohexane: 30/70). 10 g of oil are obtained. Yd.=66%. 1 H NMR: 1,1 (d,2H); 1.6-3.2 (m,11H); 3.50 (t,2H); 5.3 (s,1H); 6.80-7.45 (m,8H)

The synthetic route of 4629-78-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Cooperation Pharmaceutique Francaise; US5846980; (1998); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.189333-49-1,3-Benzyl-3,9-diazaspiro[5.5]undecane,as a common compound, the synthetic route is as follows.

To 5-fluoro-2-nitroanisole (1.0 kg, 5.84 mol, 1 equivalent) and3-Benzyl-3,9-diaza-spiro [5.5] undecane (1.70 kg, 5.57 mol, 0.95 equivalent)After adding N, N-diisopropylethylamine (1.13 kg, 8.77 mol, 1.55 equivalents) to a solution of N-methylpyrrolidone (4 L), the reaction solution was stirred at 100 C for 4 hours.TLC (dichloromethane: methanol = 6: 1, Rf = 0.5) showed that the reaction was complete. After the reaction solution was cooled to room temperature, water (16L) was slowly added to the reaction solution, and a large amount of solids precipitated. The suspension was stirred for 1 hour and then filtered. The filter cake was added to ethanol (5L), and refluxed for 1 hour.After cooling to room temperature, it was filtered. After the filter cake was re-slurried with ethanol (5L) under reflux,It was then filtered and the filter cake was dried to give the product (1.92 kg, 83% yield) as a yellow solid.

189333-49-1, The synthetic route of 189333-49-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Qilu Pharmaceutical Co., Ltd.; Lin Dong; Zhou Guangqiang; Li Shubin; Wang Xin; Zhang Zhantao; Liu Zhen; Wang Xinsheng; (30 pag.)CN110407877; (2019); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

5773-58-0, 3-Methylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5773-58-0, The mixture of compound A0056-1 (115 mg, 1.02 mmol), compound 1 (323 mg, 1.53 mmol) and H2O (0.3 mL) was stirred overnight (about 18 hours) at room temperature. Thin-layer chromatography was used to monitor the reactions progress. The reaction mixture was quenched by extraction with ethyl acetate, followed by a washing with water and brine. The quenched reaction mixture was dried with anhydrous sodium sulfate and concentrated under vacuum to afford 300 mg of crude product as yellow oil. The crude product was purified via column chromatography to obtain 20 mg of the title product as colorless oil (yield: 6%) . The structure was confirmed by 1H NMR and MS.

The synthetic route of 5773-58-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PAIN THERAPEUTICS, INC.; WO2010/51374; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

14813-01-5, 1-Benzylpiperidin-3-ol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-Benzyl-3-piperidinol (600 g), toluene (6 L), ethyl acetoacetate (490.2 g), boric acid (19.5 g) were added to a 10 L reaction flask. Heated to reflux overnight, HPLC detection, The remaining 2-6.2% of 3-benzyl-3-piperidinol was added to the atmospheric distillation apparatus to distill off the ethanol produced by the reaction. Complete the reaction in 2 hours, cool to 0~10 C, adjust the pH to about 3, and extract the product with water (1 L × 2). The aqueous phase was combined, and the pH of the aqueous phase was adjusted to about 7 and extracted with ethyl acetate (1L×2). Wash with saturated brine (500 mL×2), dry over anhydrous sodium Concentrated to dryness afforded 786.1 g of a yellow oil., 14813-01-5

As the paragraph descriping shows that 14813-01-5 is playing an increasingly important role.

Reference：
Patent; Tianjin Changyuan Pharmaceutical Technology Co., Ltd.; Chi Fangfei; Ying Zixiang; Liu Wenjuan; Mo Lan; (9 pag.)CN104529872; (2018); B;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

4-methylpiperidin-4-yl)methanol (E4) (2.4 g, a mixture of the amino alcohol and NH4CO2H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 hr at room temperature, IN HCl (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under high vacuum. The product obtained is an analytically pure oil (E5) and used without further purification. LC/MS m/z (M+l) 202.2, retention time 1.89 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). 1H NMR (400 MHz, DMSO-d6) delta 4.05 (q, J = 7.1 Hz5 2H), 3.66 {at, J= 13.6, 4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, J = 5.2 Hz, IH), 3.11 (dd, J= 23.9, 3.5 Hz, IH), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J = 7.1 Hz, 3H), 0.93 (s, 3H)., 297172-16-8

The synthetic route of 297172-16-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/100670; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.138377-80-7,3-Aminopiperidin-2-one hydrochloride,as a common compound, the synthetic route is as follows.

Example 10 ; 3-[({4-[(3-chloro-2-fluorophenyl) amino]-7-methoxyquinazolin-6- yl} methyl) amino] piperidin-2-one; (Process (a)); 4- [ (3-Chloro-2-fluorophenyl) amino]-7-methoxyquinazoline-6-carbaldehyde was coupled with 3-amino-piperidin-2-one (prepared by converting 3-amino-piperidin-2-one hydrochloride to the free-base form) using an analogous method to that described for the equivalent step in Example 1 to give the title compound ; 1H NMR spectrum : (DMSO d6) 1. 5= (m, 1H), 1.68 (m, 1H), 1.84 (m, 1H), 2.16 (m, 1H), 2.73 (brs, 1H), 3.05 (dd, 1H), 3.13 (m, 2H), 3.84 (d, 1H), 3.93 (d, 1H), 3.98 (s, 3H), 7.21 (s, 1H), 7.28 (t, 1H), 7.48 (t, 1H), 7.53 (m, 2H), 8.35 (s, 1H), 8.44 (s, 1H), 9.80 (s, 1H); Mass Spectrum : (M+H) +430., 138377-80-7

The synthetic route of 138377-80-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/75439; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem