Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.187834-88-4,1-Boc-isonipecoticacidhydrazide,as a common compound, the synthetic route is as follows.

3-phenyl-2-(4-{ [4-(5-pyrimidin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl} phenyl)-l,6-naphthyridin-5(6H)-one hydrochloride (6-54) 2-(3-piperidin-4-yl-lH-l,2,4-triazol-5-yl)pyrimidine (B)A mixture of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (10.1 g, 41.5 mmol) and 2-cyanopyrimidine (4.36 g, 41.5 mmol) in 1-butanol (20 mL) was heated to reflux for 48 hours. The mixture was concentrated, suspended in ether, and filtered to give tert-butyl 4-(5-pyrimidin-2- yl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate as a solid. MS (M+Eta1″): 331.2 observed; 1H-NMR (400 MHz, CD3OD): delta 8.92 (d, J=4.0Hz, 2H), 7.52 (t, J=4.0Hz, IH), 4.18-4.15 (m, 2H), 3.14-3.08 (m, IH), 2.98 (br.s, 2H), 2.07-2.01 (m, 2H), 1.85-1.77 (m, 2H), 1.48 (s, 9H)., 187834-88-4

The synthetic route of 187834-88-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2006/65601; (2006); A2;,
Piperidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15883-20-2,N-(2′,6′-Dimethylphenyl)-2-piperidinecarboxamide,as a common compound, the synthetic route is as follows.

To 1L four reaction flask was added 500g of toluene, then add 100g of starting material,Then add 1.01 ~ 1.05 equivalent of anhydrous potassium carbonate, then add 2% to 6% tetrabutylammonium bromide,Then add 1.1 to 1.3 times the equivalent of n-butyl bromide, and slowly warmed to 80 ~ 85 , incubated for 5 hours,Cooled to room temperature, filtered, the filtrate was transferred to a 1L four-necked flask,Hydrogen chloride gas is passed into the filtrate until it is no longer absorbed, filtered, the filter cake washed with toluene,Dried to give bupivacaine hydrochloride 132.84 ~ 141.70g,HPLC content> 99%, yield 90% ~ 96%., 15883-20-2

The synthetic route of 15883-20-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Jiangsu Tianhe Pharmaceutical Co., Ltd.; Wang Lei; Liu Lei; Zhao Yunde; Wang Zhiquan; Zhu Linfei; (9 pag.)CN106117118; (2016); A;,
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20845-34-5, 1-Methyl-2-piperidinemethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of 2-(hydroxymethyl)-1-(2-isothiocyanatoethyl)-1-methylpiperidin-1-ium trifluoromethanesulfonate: A solution of 2-Isothiocyanatoethyl trifluoromethanesulfonate (30.2 mg, 0.128 mmol) and (1-methylpiperidin-2-yl)methanol (17.4 mg, 1.05 eq.) in toluene (0.5 mL) was stirred at RT for 2 hrs. The solvent was decanted and the residual oil was dissolved in DCM (0.3 mL) and Et2O (diethyl ether) (1 mL) was added to precipitate the salt. The top solvent layer was decanted. This process repeated twice. The residue was dried in high vacuum to give 41.9 mg (89.7percent) as colorless oil. MS-ESI: 129.84 (M-CH2CH2NCS?OTf?), 215.07 (M-OTf?), 20845-34-5

The synthetic route of 20845-34-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The Procter & Gamble Company; GARCIA-GARCIA, Jose Carlos; HAZEN, Stanley Leon; WOS, John August; (43 pag.)US2017/152222; (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.184637-48-7,tert-Butyl 3-aminopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of 3-((terf-butoxycarbonyl)amino)piperidine (400 mg, 2.0 mmol) in DCM (10 mL) was added triethylamine (0.50 mL, 3.6 mmol) followed by methyl chloroformate (0.20 mL, 2.6 mmol). After stirring overnight, the reaction was concentrated, diluted with EtOAc and washed with 0.5 N HCI, water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound as a white solid (502 mg, 97percent yield). 1H NMR (400 MHz, CD3SOCD3) delta 1 .27-1 .35 (m, 2 H), 1 .38 (s, 9 H), 1 .62-1 .69 (m, 1 H), 1 .72-1 .80 (m, 1 H), 2.74-2.83 (m, 1 H), 3.20-3.28 (m, 1 H), 3.52-3.58 (m, 1 H), 3.58 (s, 3 H), 3.66-3.74 (m, 1 H), 3.76-3.89 (m, 1 H), 6.85-6.91 (m, 1 H)., 184637-48-7

The synthetic route of 184637-48-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103816-19-9,[1,4′-Bipiperidine]-1′-carbonyl chloride,as a common compound, the synthetic route is as follows.

Embodiment of the Invention Preparation Examples Preparation Example 1; Preparation of 10-((4′-piperidylpiperidine)carbonyloxy)-9-allylcamptothecin(CPT-4); One gram (1.25 equivalent weight) of piperidylpiperidine chloroformic acid amide (compound 8) was dissolved in 70mL of dichloromethane, 10-hydroxy-9-allylcamptothecin (1g, 1 equivalent weight) was dissolved in 70mL of anhydrous pyridine, and then the above dichloromethane solution was added into the anhydrous pyridine solution under cooling condition. After the reaction was completed, the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and 1.25g of CPT-4 yellow solid was obtained. 1HNMR (DMSO-d6) (ppm) : 1.01 (3H, t), 1.58?1.90 (10H, m), 1.80?1.99 (2H, m), 2.89 (4H, b), 3.09 (1H, b), 3.71 (2H, d), 4.45 (2H, dd), 4.94 (1H, dd), 5.11 (1H, dd), 5.14 (2H, s), 5.15 (1H, d), 5.66 (1H, d), 6.00 (1H, m), 7.47 (1H, d), 7.65 (1H, s), 8.11 (1H, d), 8.51 (1H, s).

103816-19-9, The synthetic route of 103816-19-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; EP1995249; (2008); A1;,
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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.1089279-91-3,1-(4-Amino-3-methoxyphenyl)-N,N-dimethylpiperidin-4-amine,as a common compound, the synthetic route is as follows.

To n-butanol (2 mL) was added compound 4A-5 (50 mg, 0.200 mmol) and compound 5A-2 (70 mg, 0.200 mmol), and then p-toluenesulfonic acid (35 mg, 0.200 mmol) was added under stirring. The mixture was heated to 100C and stirred for 5 hours. After TLC indicated the reaction was completed, the reaction mixture was concentrated under reduced pressure to give a crude product, which was further purified and isolated by column chromatography to obtain an off-white solid product, compound I-6 (78 mg, yield 69.4%). 1H NMR (400 MHz, cd3od) delta 9.11 (d, J=6.9 Hz, 1H), 8.36-8.31 (m, 1H), 8.09 (d, J=3.6 Hz, 1H), 7.58-7.45 (m, 2H), 6.67 (t, J=2.8 Hz, 1H), 6.57-6.50 (m, 1H), 3.92-3.76 (m, 6H), 3.40-3.31 (m, 1H), 2.90 (s, 6H), 2.79 (m, 2H), 2.18 (m, 2H), 1.87 (m, 2H), 1.29 (t, J=6.6 Hz, 6H). LCMS: t=0.807 min, 559.2 (M), 560.2 (M+1)

1089279-91-3, The synthetic route of 1089279-91-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Humanwell Healthcare (Group) Co., Ltd.; WANG, Xuehai; XU, Yong; SHENG, Xijun; ZHANG, Xiaolin; XIA, Hangui; YANG, Zhongwen; YUE, Yang; HUANG, Lu; XIAO, Qiang; (80 pag.)EP3372594; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.92197-36-9,1-Benzyl-4-(hydroxymethyl)piperidin-4-ol,as a common compound, the synthetic route is as follows.

92197-36-9, step 1 4- (hydroxymethyl) piperidin-4-ol hydrochloride1-benzyl-4- (hydroxymethyl) piperidin-4-ol 500 mg (J. Med. Chem., was dissolved in ethanol 10ml synthesis) according to 1988,486-491, 10% palladium-carbon 300mg and concentrated hydrochloric acid 0.38ml was added and overnight hydrogenated at room temperature.Insoluble matter was separated by filtration, and washed with ethanol and water, and the filtrate was concentrated under reduced pressure.To the residue was powdered addition of diethyl ether, the desired product was obtained 374mg as a white powder.

As the paragraph descriping shows that 92197-36-9 is playing an increasingly important role.

Reference£º
Patent; NIPPON SHINYAKU COMPANY LIMITED; FUJIHARA, HIDETAKA; ASAKI, TETSUO; HORI, KATSUTOSHI; NAITO, HARUNA; (146 pag.)JP5668756; (2015); B2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.392331-89-4,1-Boc-3-methylaminopieridine,as a common compound, the synthetic route is as follows.

3-(N-Acetyl-N-methylamido)piperidine was prepared from N3-Cbz protected 3-amino-piperidine-1-carboxylic acid t-butyl ester (De Costa, B., et al. J. Med. Chem. 1992, 35, 4334-43) after four synthetic steps: i) MeI, n-BuLi, THF, -78 C. to rt; ii) H2 (1 atm), 10% Pd/C, EtOH; iii) AcCl, i-Pr2NEt, CH2Cl2; iv) CF3CO2H, CH2Cl2. m/z: [M+H]+calcd for C8H16N2O: 157.13; found, 157.2. 1H-NMR (CD3OD; TFA salt): delta (ppm) 4.6 (m, 1H), 3.3 (m, 1H), 3.2 (m, 1H), 3.0 (m, 1H), 2.9 (s, 3H), 2.8 (m, 1H), 2.0 (s, 3H), 1.9-1.7 (m, 4H)., 392331-89-4

The synthetic route of 392331-89-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THERAVANCE, INC.; US2006/100426; (2006); 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.561314-57-6,2,8-Diazaspiro[4.5]decan-3-one,as a common compound, the synthetic route is as follows.,561314-57-6

To a solution of ethyl 5-oxo-2-azabicyclo[2.2.2]octane-2-carboxylate (6.70 g, 34 mmol)and 2,8-diazaspiro[4.5]decan-3-onel (5.24 g, 34 mmol) in DMF (30 mL) was addedHOAc (2.9 mL, 51 mmol) under nitgogen, the reaction mixture was stirred at rt for 20mi Na(OAc)3BH (21.60 g,102 mmol) was added and the reaction was stirred at45 0Cfor 3 d. Then the reaction mixture was warmed to 60 0C and stirred for another 24 h.The solvent was removed in vacuo and the residue was dissolved in water (20 mL)and basified with sat.NaHCO3. The aqueous layer was concentrated to dryness andthe resulting white solid was diluted with DCM (100 mL). The suspension was stirred atrt for 30 mm, filtered and the filter cake was washed with DCM (4 x 25 mL). Theorganic layers were combined and the solvent was removed in vacuo. The residuewas purified by preparative reversed phase HPLC (Instrument: Gilson, Column:Xbridge 21 .2*250 mm C18, 10 um; Mobile Phase: A: water (10 mMol/L NH4HCO3) B:CAN); Flow rate(ml/min): 25.00) to give the two racemic isomers of ethyl 5-(3-oxo-2,8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate. Which were furtherpurified by chiral SFC (Column: OJ-H, 4.6*250mm; Co-solvent: MeOH(0.1% NH4OH);column temperature: 40;C02 flow rate: 2.55) to give ethyl 5-(3-oxo-2,8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate, Example 3-1 Isomer1 (0.78 g, 6.9%) as a colourless solid, ethyl 5-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)-2-azabicyclo[2.2.2]octane-2-carboxylate, Example 3-1 Isomer 2 (1.20 g, 10.5%) as acolourless solid, ethyl 5-(3-oxo-2, 8-diazaspi ro[4. 5]dec-8-yl)-2-azabicyclo[2 .2 .2]octane-2-carboxylate, Example 3-1 Isomer 3 (0.45 g, 3.9%) as a colourless solid and ethyl 5-(3-oxo-2, 8-diazaspiro[4. 5]dec-8-yl)-2-azabicyclo[2 .2.2]octane-2-carboxylate, Exam pie3-1 isomer 4 (1.30 g, 11.4%) as a colourless solid.

The synthetic route of 561314-57-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HEPTARES THERAPEUTICS LIMITED; CONGREVE, Miles Stuart; BROWN, Giles Albert; TEHAN, Benjamin Gerald; PICKWORTH, Mark; CANSFIELD, Julie Elaine; (105 pag.)WO2015/140559; (2015); A1;,
Piperidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.154775-43-6,3-(1-(tert-Butoxycarbonyl)piperidin-4-yl)propanoic acid,as a common compound, the synthetic route is as follows.,154775-43-6

(a) Di-t-butyl [[4-[[N-[3-(1-t-butyloxycarbonylpiperidin-4-yl)propionyl]-N-methylamino]acetyl]-o-phenylene]dioxy]diacetate 3-(1-t-butyloxycarbonylpiperidin-4-yl)propionic acid (257 mg), di-t-butyl [[4-[(N-methylamino)acetyl]-o-phenylene]dioxy]diacetate hydrochloride (446 mg), N-methylmorpholine (101 mg), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 442 mg), and a catalytic amount of 4-dimethylaminopyridine were dissolved in 5 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 hours. After ethyl acetate (100 ml) was added to the reaction mixture, the resulting mixture was washed with water. The solvents were removed under reduced pressure. The residual mixture was purified by column chromatography on silica gel to give 285 mg of the title compound from the fraction eluted with n-hexan:ethyl acetate=3:1. 1 H-NMR (CDCl3) delta: 1.04-1.15 (m, 2H), 1.38-1.54 (m, 28H), 1.54-1.75 (m, 4H), 2.35-2.48 (m, 2H), 2.58-2.75 (m, 2H), 3.08 (s, 3H), 3.98-4.29 (m, 2H), 4.62 (s, 2H), 4.66 (s, 2H), 4.77 (s, 2H), 6.82 (d, J=8 Hz, 1H), 7.47 (s, 1H), 7.60 (d, J=8 Hz, 1H). SIMS (m/z): 649 (M+ +1).

The synthetic route of 154775-43-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Meiji Seika Kabushiki Kaisha; US5594004; (1997); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem