Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62718-31-4,1-Benzylpiperidine-4-carbonitrile,as a common compound, the synthetic route is as follows.

62718-31-4, Benzylprotection of 1 to give 5 was achieved in 70-80% yield by reductive amination with benzaldehyde and sodium triacetoxyborohydride as the reducing agent in DCM as the solvent. Dehydration to the cyano compound 6 was performed under the same conditions as given for the preparation of 3. Subsequently, compound 6 was reacted with either benzylmagnesiumchloride or phenylmagnesiumchloride at rt overnight, followed by hydrolysis with 2M sulfuric acid to give the ketones 7 and 8, respectively, which were reductively aminated with benzylamine in ethanol in the presence of Pd/C (10%) at 3bar hydrogen pressure overnight in yields of 60-80% to the templates 9 and 10, respectively, which were used as racemates in the following synthetic steps. c) To a solution of l-benzyl-4-cyano-piperidine (9.3 g) in THF (90 ml) was added a solution of benzylmagnesiumchloride (1. 3 M in THF, 57 ml ; Fluka) at rt. Copper bromide was added (150 mg) and the reaction mixture was warmed to 60C for 8 h. The mixture was quenched by the addition of water (10 ml) and 15% sulfuric acid (65 ml) and stirring continued for 30 min. The THF was evaporated and 15% sodium hydroxide solution was added until the pH of the aqueous phase reached 8. The product was extracted with ether (2 x) to give crude material (10.8 g) which was purified by bulb-to-bulb destillation to give l- (l-benzyl- piperidin-4-yl)-2-phenyl-ethanone (5.1 g) as a colorless, viscous liquid.

62718-31-4 1-Benzylpiperidine-4-carbonitrile 793383, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; ACTELION PHARMACEUTICALS LTD; WO2004/2483; (2004); A1;,
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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 5. PREPARATION OF HEMI FUMARATE OF 3-BENZYL-S^-DIAZASPIRO[S-S]UNDECANEThis Example illustrates the preparation of the hemi fumarate of 3-benzyl-3,9- diazaspiro [5.5]undecane :Crude 3-benzyl-3,9-diazaspiro[5.5]undecane (72.1 g, 0.295 mol) (from Example 4) is suspended in wo-propanol (200 mL) and heated at 65 0C under nitrogen to form a clear Solution B. Fumaric acid (17. Ig, 0.147 mol) is suspended in wo-propanol (190 mL) and reflux to form a clear Solution A. Solution A is added to Solution B in one portion while stirring under nitrogen. The resulting clear solution becomes cloudy in a minute and more precipitate forms. The heat bath is removed and resulting mixture is stirred overnight under nitrogen. The mixture is filtered under nitrogen and washed with small amount of wo-propanol (-60 mL). The product is dried under high vacuum to give the title compound as a white loose powder. 74.5 g (yield 83.5%, and overall yield in 76%). LC-MS (M+l) 245.12; Rtau = 1.54 min. 1H NMR (CD3OD) 1.60-1.72 (m, 8H), 2.50-2.60 (m, 4H), 3.10-3.16 (m, 4H), 3.64 (s, 2H), 6.64 (s, IH), 7.26-7.38 (m, 5H).

189333-49-1, As the paragraph descriping shows that 189333-49-1 is playing an increasingly important role.

Reference：
Patent; NEUROGEN CORPORATION; XU, Yuelian; XIE, Linghong; HAN, Bingsong; MAYNARD, George D.; CHENARD, Bertrand, L.; STAAB, Andrew J.; WO2009/97405; (2009); A2;,
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25137-01-3, (R)-Ethyl piperidine-3-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Chlorobenzenesulfonyl chloride (0.25 mL, 1.8 mmol) was added to a solution of (R)-(+)-nipecotic acid ethyl ester (available from Aldrich Chemical Company; Inc., Milwaukee, Wisc.; 250 mg, 1.6 mmol) and triethylamine (0.5 mL, 3.6 mmol) in dichloromethane (5 mL) under argon. An additional portion of dichloromethane (10 mL) was added and the solution was stirred for five days at room temperature. The reaction mixture was washed with water and the water layer was back-extracted with dichloromethane. The combined organic layers were washed with 80% saturated brine, dried (magnesium sulfate), filtered and evaporated to give (3R)-1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylic acid ethyl ester (561 mg) as a colorless viscous oil, which was used directly in the next step. NMR indicated the presence of the desired product along with a small amount of dichloromethane.

25137-01-3, 25137-01-3 (R)-Ethyl piperidine-3-carboxylate 185582, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Gillespie, Paul; Goodnow, Robert Alan; Kowalczyk, Agnieszka; So, Sung-Sau; Zhang, Qiang; US2006/199816; (2006); A1;,
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885279-92-5, 1-Boc-1,8-diaza-spiro[4.5]decane is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 142: 1,1,1,3,3,3-Hexafluoropropan-2-yl 1-((1-acetyl-1,2,3,4-tetrahydroquinolin-8- yl)methyl)-1,8-diazaspiro[4.5]decane-8-carboxylate Step 1: Preparation of 1-tert-butyl 8-(1,1,1,3,3,3-hexafluoropropan-2-yl) 1,8- diazaspiro[4.5]decane-1,8-dicarboxylat A flask was charged with triphosgene (2.46 g, 8.29 mmol, 0.50 equiv), DCM (100 mL) and HFIP (4.21 g, 24.9 mmol, 1.50 equiv). DIEA (6.45 g, 49.7 mmol, 3.00 equiv) was added dropwise at 0 ^C. The reaction mixture was stirred for 2 h at 0 ^C. tert-Butyl 1,8- diazaspiro[4.5]decane-1-carboxylate (4.01 g, 16.6 mmol, 1.00 equiv) was added, and the reaction was stirred for 3 h at 0 ^C before quenching with H2O (50 mL). The mixture was extracted with DCM (3 x 50 mL) and the organic layers were combined, washed with H2O (3 x 100 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified on a silica gel column (1:2 EtOAc/petroleum ether) to provide 4.34 g (60% yield) of 1-tert-butyl 8-(1,1,1,3,3,3- hexafluoropropan-2-yl) 1,8-diazaspiro[4.5]decane-1,8-dicarboxylate as a white solid. LCMS (ESI, m/z): 435 [M+H]+.

885279-92-5, As the paragraph descriping shows that 885279-92-5 is playing an increasingly important role.

Reference：
Patent; ABIDE THERAPEUTICS, INC.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; CISAR, Justin S.; GRICE, Cheryl A.; JONES, Todd K.; WEBER, Olivia D.; (277 pag.)WO2017/197192; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4801-58-5,Piperidin-1-ol,as a common compound, the synthetic route is as follows.

General procedure: To a 25-mL flask equipped with a magnetic stirrer, in which the air was replaced by N2, was added CuBr (0.05 mmol), toluene (1.0 mL), aldehyde (1.0 mmol), alkyne (1.5 mmol), and hydroxylamine (1.5 mmol). The mixture was stirred at 70C. After the completion of the reaction (monitored by TLC), the reaction solution was submitted to flash chromatographic separation on silica gel using petroleum ether/ethyl acetate as an eluent to give the corresponding product.

4801-58-5, 4801-58-5 Piperidin-1-ol 20935, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Guo, Na; Ji, Jian-Xin; Tetrahedron Letters; vol. 53; 36; (2012); p. 4797 – 4801;,
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4629-80-5, 1,3-Dimethylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 14 6-chloro-3-(1,3-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 0.97 gm (6.4 mMol) 6-chloro-1H-indole and 1.6 gm (13.0 mMol) 1,3-dimethyl-4-piperidone, 1.05 gm (63%) of the title compound were recovered as a crystalline solid. m.p.=170-172 C. MS(FD): m/e=260 (M+) EA: Calculated for: C15 H17 N2 Cl: Theory: C, 69.09; H, 6.57; N, 10.74. Found: C, 69.39; H, 6.40; N, 10.97., 4629-80-5

Big data shows that 4629-80-5 is playing an increasingly important role.

Reference：
Patent; Eli Lilly and Company; US5846982; (1998); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1187173-43-8,2,7-Diazaspiro[4.5]decan-1-one hydrochloride,as a common compound, the synthetic route is as follows.

Preparation 44: tert-butyl 1-oxo-2,7-diazaspiro[4,5]decane-7-carboxylate (P44)2,7-diazaspiro[4.5]decan-l-one hydrochloride (600 mg, 3.15 mmol), was dissolved in 30 m L of DCM. To this solution, TEA (1.98 mL, 14.18 mmol) and Boc20 (895 mg, 4.10 mmol) were added and the reaction mixture was stirred at RT for 4 hrs. Water was added and the two layers were separated; the organic layer was washed with NH4CI, dried and evaporated to obtain ferf-butyl l-oxo-2,7- diazaspiro[4.5]decane-7-carboxylate (p44, 830 mg, y= quant.), colourless oil.MS (ES) (m/z): 255.2 [M+H]+.

1187173-43-8, As the paragraph descriping shows that 1187173-43-8 is playing an increasingly important role.

Reference：
Patent; SHIRE INTERNATIONAL GMBH; SEMERARO, Teresa; TARSI, Luca; MICHELI, Fabrizio; LUKER, Tim; CREMONESI, Susanna; (122 pag.)WO2016/42451; (2016); A1;,
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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.

69B. tert-Butyl 3-(4-((4-(hydroxymethyl)-4-methylpiperidin-1-yl)methyl)-3-methylphenoxy)azetidine-1-carboxylate To a solution of 69A (3.00 g, 10.3 mmol) in DCM (50 mL) was added (4-methylpiperidin-4-yl)methanol (2.56 g, 15.5 mmol) followed by DIPEA (3.60 mL, 20.6 mmol). The reaction mixture was stirred at RT for 20 min and then sodium triacetoxyborohydride (6.55 g, 30.9 mmol) was added. The mixture was stirred at RT overnight and then washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted several times with DCM. The organic layers were filtered through a phase separator and then evaporated. There was obtained 3.1 g (74%) of the product as an oil. 1H NMR (500 MHz, CDCl3): delta 0.95 (s, 3H), 1.33 (m, 2H), 1.45 (s, 9H), 1.51 (m, 2H), 2.26 (m, 2H), 2.30 (s, 3H), 2.51 (m, 2H), 3.38 (s, 2H), 3.39 (s, 2H), 3.99 (m, 2H), 4.27 (m, 2H), 4.84 (m, 1H), 6.48 (dd, 1H), 6.56 (d, 1H), 7.16 (d, 1H), MS (APCI+) m/z 405 [M+H]+.

297172-16-8, As the paragraph descriping shows that 297172-16-8 is playing an increasingly important role.

Reference：
Patent; AstraZeneca AB; US2012/10189; (2012); A1;,
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3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A 1-benzyl-4-(methylamino)piperidine A solution of 1 mol of N-benzylpiperid-4-one in 2200 cm3 of isopropanol is cooled to 18 C. A freshly prepared solution of 3 mol of methylamine in 300 cm3 of methanol is added to the first solution. The mixture is left at that temperature for one hour. 1.66 mol of sodium hydroxide in the form of pellets are added. 1.37 mol of sodium borohydride are added at a constant temperature of 18 C. The mixture is allowed to return to room temperature and then the reagents are left in contact for 12 hours. The solvents are evaporated, and the residue is taken up in ether and then washed with water. Drying and evaporation yield an oil which is the desired compound. Yield: 78%., 3612-20-2

3612-20-2 1-Benzylpiperidin-4-one 19220, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Adir et Compagnie; US5298503; (1994); A;,
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35856-62-3, Piperidine-1-sulfonyl chloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 25 Piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide A solution of 6-propyl-pyridin-2-ylamine (0.2 g) and piperidine-1-sulfonyl chloride (0.296 g, Bull. Soc. Chim. Fr.; 1936, 2143) in pyridine (7 mL) was heated to reflux for 15 h. After concentration of the reaction mixture in vacuo the residue was taken up in EtOAc, which was then washed with 1N aqueous HCl, saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc/toluene (9:1 to 1:1) as eluent. Combination of the purified fractions and concentration in vacuo gave the desired piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide (0.133 g) as a colorless amorphous solid. MS (ESI-): 282.0 ([M-H]-)., 35856-62-3

The synthetic route of 35856-62-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Amrein, Kurt; Hunziker, Daniel; Kuhn, Bernd; Mayweg, Alexander; Neidhart, Werner; US2006/74237; (2006); A1;,
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