Category: piperidines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10315-06-7,Methyl 1-benzylpiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.

1.5 (1-Benzylpiperidin-4-yl)-N-methoxy-N-methylcarboxamide A solution of 4.17 g (42.8 mmol) of N,O-dimethylhydroxylamine hydrochloride in 195 mL of THF is cooled to -20 C., and 6.51 g (28 mmol) of methyl (1-benzylpiperidin-4-yl)carboxylate are added. Next, 85 mL of a 1M solution of isopropylmagnesium bromide in THF are added over 20 minutes while keeping the temperature in the region of 5 C. The mixture is stirred at -10 C. for 20 minutes. The reaction medium is hydrolyzed with 40 mL of 20% ammonium chloride solution and then extracted with ethyl acetate. The combined organic phases are washed with water and with brine, and then dried over anhydrous sodium sulfate and evaporated under reduced pressure. 6.9 g of an oily product are obtained.1H NMR (DMSO-d6, 250 MHz) delta ppm: 1.5-1.75 (m, 4H); 1.9-2.05 (m, 2H); 2.55-2.7 (m, 1H); 2.8-2.9 (m, 2H); 3.09 (s, 3H); 3.46 (s, 2H); 3.67 (s, 3H); 7.2-7.4 (m, 5H).

10315-06-7, As the paragraph descriping shows that 10315-06-7 is playing an increasingly important role.

Reference：
Patent; SANOFI-AVENTIS; US2009/124624; (2009); 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.690261-64-4,2-(Piperidin-4-yl)pyrimidine hydrochloride,as a common compound, the synthetic route is as follows.

A solution of EDC.HCI (ALFA-AESAR, 340 mg, 1.77 mmol), TEA (ALFA-AESAR, 0.25 mL, 1 .77 mmol), HOBt (ALDRICH, 240 mg, 1 .77 mmol), Intermediate 30 (295.3 mg, 1.48 mmol) and 4,4,4-trifluorobutyric acid (ALFA-AESAR, 252 mg, 1.77 mmol) in DMF (15 mL) was stirred at rt overnight. The mixture was then washed with NaHCC>3 saturated solution and EtOAc was added, the two phases were separated and the aqueous one was further extracted with EtOAc. The collected organic layer was dried(anh) Na2SC>4, filtered and evaporated. The crude so obtained was purified by flash chromatography (Si SNAP 50, CyHex EtOAc from 1/1 to 0/10, then DCM/MeOH 8/2) to give title compound (141 mg, 33%) as a white solid. 1H NMR (500 MHz, DMSO-de) delta ppm: 8.75 (d, J = 4.9 Hz, 2H), 7.35 (t, J = 4.9 Hz, 1 H), 4.44 (d, J = 13.2 Hz, 1 H), 3.94 (d, J = 13.7 Hz, 1 H), 3.22-3.13 (m, 1 H), 3.13-3.05 (m, 1 H), 2.82-2.72 (m, 1 H), 2.70-2.57 (m, 2H), 2.57-2.45 (m, 2H), 2.02-1.90 (m, 1 H), 1.79-1.67 (m, 1 H),1.65-1.51 (m, 1 H). [ES+ MS] m/z 288 (MH+)., 690261-64-4

690261-64-4 2-(Piperidin-4-yl)pyrimidine hydrochloride 56965759, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIOVERSYS AG; PORRAS DE FRANCISCO, Esther; REMUINAN-BLANCO, Modesto Jesus; BOUROTTE, Marilyne; DEPREZ, Benoit; WILLAND, Nicolas; (89 pag.)WO2019/34701; (2019); 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.1158759-06-8,tert-Butyl 3-amino-3-methylpiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 5. tert-Butyl 3-methyl-3-((7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate. tert-Butyl 3-amino-3-methylpiperidine-1-carboxylate (3.3 g, 15.398 mmol) and tert-butyl 3-amino-3-methylpiperidine-1-carboxylate (3.9 g, 12.7 mmol) was stirred at 140 C. overnight. After TLC showed tert-butyl 3-amino-3-methylpiperidine-1-carboxylate to be consumed, the mixture was diluted with DCM (80 ml). The DCM layer was washed with sat NaHCO3 (aq) and brine and concentrated to dryness to give crude product which was purified by chromatography (silica, EtOAc/Petroleum ether, 0-40%) to give tert-butyl 3-methyl-3-((7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (2.4 g, 40%) as a white solid

1158759-06-8, 1158759-06-8 tert-Butyl 3-amino-3-methylpiperidine-1-carboxylate 20816952, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

914988-10-6,914988-10-6, tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N,N-diisopropylethylamine (8 mL, 46.0 mmol) was added to a mixture of (2,6-diethylphenyl)hydrazine hydrochloride (8 g, 39.9 mmol), tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate (5 g, 22.3 mmol) and EtOH (60 mL) in a 250 mL round bottom flask under magnetic stirring. The resulting mixture was stirred under reflux for 3 h. Glacial acetic acid (12 mL, 208 mmol) was added and the mixture was stirred under reflux for another 2 h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc and washed with NaOH solution (2 N), brine, and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by silica gel flash chromatography (5 to 55% EtOAc in hexanes) to give tert-butyl 3-amino-2-(2,6-diethylphenyl)-6,7-dihydro-2H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate. MS: (ES) m/z calculated for C21H31 N4O2 [M+H]+ 371.2, found 371.2.

As the paragraph descriping shows that 914988-10-6 is playing an increasingly important role.

Reference：
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LUI, Rebecca M.; SINGH, Rajinder; MALI, Venkat Reddy; ZENG, Yibin; ZHANG, Penglie; US2019/300526; (2019); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 4-Bromomethylpiperidine-1-carboxylic Acid Benzyl Ester To a solution of 4-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (1.11 g), carbon tetrabromide (1.77 g) in methylene chloride (11 ml) was added triphenylphosphine (1.4 g) with ice-cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=10:1) and dried under reduced pressure to give the title compound (1.25 g). 1H-NMR (delta ppm, CDCl3) 1.05-1.30 (m, 2H), 1.70-1.90 (m, 3H), 2.78 (m, 2H), 3.29 (d, 2H), 4.10-4.30 (m, 2H), 5.13 (s, 2H), 7.26-7.38 (m, 5H)., 122860-33-7

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference：
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

936130-82-4, Methyl 4-(piperidin-4-yl)benzoate hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

936130-82-4, Step 3 : Preparation of methyl 4-[ 1 -[4-methyl-3-(pyridine-4- carbonylamino)benzoyl]-4-piperidyl]benzoate; A suspension of methyl 4-(4-piperidyl)benzoate hydrochloride (5 g, 22.8 mmol), 4-methyl- 3-(pyridine-4-carbonylamino)benzoic acid [see below] (5.87 g, 22.8 mmol, 1 eq) and DMAP (6.13 g, 50.2 mmol, 2.2 eq) in DCM (80 mL) was treated with EDAC (5.25 g, 27.36 mmol, 1.2 eq), and the reaction mixture was stirred overnight under argon at ambient Q temperature. The reaction mixture was then concentrated in vacuo and the product purified by flash column chromatography (Companion , 2x12Og silica columns, eluting with a gradient of 5-7% MeOH in DCM) to give the title compound as a colourless solid (9.54 g, 91% yield), 1H NMR (400.132 MHz, MeOD) delta 1.83 (bs, 2H), 1.95 (bs, IH), 2.09 (bs, IH), 2.40 (s, 3H), 3.00 (bs, 2H), 3.31 (bs, IH), 3.95 (s, 3H), 4.13 (bs, IH), 4.90 (bs, IH), 5 7.28 (dd, IH), 7.33 (d, 2H), 7.37 (dd, IH), 7.56 (s, IH), 7.90 (d, 2H), 7.99 (d, 2H), 8.75 (d, 2H).

936130-82-4 Methyl 4-(piperidin-4-yl)benzoate hydrochloride 42614593, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59214; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

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,10338-57-5

General procedure: To a solution of an aromatic ketone (3 mmol) in EtOH (15 mL), anaromatic aldehyde (3 mmol) and KOH (3 mmol) were added and the reaction mixture was stirred for 8 h at room temperature. On completion, the reaction mixture was concentrated under vacuum, the residue was dissolved in EtOAc (30 mL) and washed with water, then brine, dried over anhydrous Na2SO4 and concentrated under vacuum to afford the target compounds, which were purified by column chromatography on silica gel (hexane/EtOAc = 7/1).

The synthetic route of 10338-57-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Fu, Dong-Jun; Zhang, Sai-Yang; Song, Jian; Liu, Yin-Chao; Zhang, Li; Zhao, Ruo-Han; Zi, Xiao-Lin; Liu, Hong-Min; Zhang, Yan-Bing; Journal of Chemical Research; vol. 40; 10; (2016); p. 620 – 623;,
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.

Example 8D (500 mg, 2.05 mmol) and Boc2O (450 mg, 2.06 mmol) in methanol mixture was added triethylamine (311 mg, 3.08 mmol) and the mixture was stirred at 20-30 deg.C for 16 hours. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate (20 mL), and washed with water (15mL × 2) and brine (20 mL) was washed, and the organic layer was dried over anhydrous sodium sulfate, and concentrated. The crude intermediate was dissolved in ethanol (15mL) and acetic acid (2mL), followed by addition of palladium hydroxide / carbon (0.1 g). The mixture was reacted under hydrogen (50Psi) for 20 hours. The mixture was filtered, the filtrate was concentrated to give the acetate salt (320 mg, 1.26 mmol, 61.37% yield) of the title compound., 189333-49-1

Big data shows that 189333-49-1 is playing an increasingly important role.

Reference：
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

89895-06-7, 1-(Piperidin-4-yl)ethanone hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,89895-06-7

Step 1: 4-acetyl-1-(benzyloxycarbonyl)piperidine To a stirred solution of 4-acetylpiperidine hydrochloride (22.6 g, 0.138 mol) in saturated aqueous Na2CO3 (100 mL), cooled to 5C, was added benzyl chloroformate (23.6 mL, 0.166 mol) dropwise over 10 – 15 min. The resulting suspension was stirred for 1/2 hour and was filtered. The solid was recrystallized from hexane (200 mL) and ethyl acetate (20 mL) producing 30.5 g of the title compound as a white solid. M.P. 87-89C.

The synthetic route of 89895-06-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK & CO., INC.; EP863757; (2003); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

948894-26-6,948894-26-6, 4-Methylpiperidine-4-carbonitrile hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

ii) 4-Methyl-l-[2-(2-phenylethoxy)ethyl]piperidine-4-carbonitrile; A mixture of the product from example 4 step (i) (2-(2~phenylethoxy)ethyl 4- methylbenzenesulfonate) (1.344 g) and the product from step (i) (4-cyano-4- methylpiperidine hydrochloride) (0.569 g) was dissolved in NMP (12 mL) and triethylamine (3 mL) added. The reaction mixture was heated at 85 0C for 3 h then allowed to CQOI and partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with further EtOAc. The combined organic extracts were washed with saturated aqueous NaHCO3, water, saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was diluted with isopropanol then loaded onto a Varian SCX column (50 g). The column was washed with isopropanol then eluted with 1:3 0.880 NH3/isopropanol to afford the sub-title compound as a brown oil which contains ~1 mole equivalent of NMP. Yield: 0.691 g1H NMR (CDCl3) delta 7.30 – 7.19 (m, 5H), 3.66 (t, 2H), 3.57 (t, 2H), 2.91 – 2.87 (m, 4H), 2.61 (t, 2H), 2.35 – 2.30 (m, 2H), 1.89 – 1.85 (m, 2H), 1.58 (td, 2H), 1.37 (s, 3H).

As the paragraph descriping shows that 948894-26-6 is playing an increasingly important role.

Reference：
Patent; ASTRAZENECA AB; WO2007/102771; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem