Month: March 2022

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;,
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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.

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;,
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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;,
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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.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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.236406-22-7,1-Boc-4-(Aminomethyl)-4-methylpiperidine,as a common compound, the synthetic route is as follows.

HATU (294 mg, 0.8 mmol) was added to the mixture of 6-methyl-7-oxo-6,7-dihydro- 1 H- pyrrolo[2,3-c]pyridine-4-carboxylic acid (Intermediate C) (135 mg, 0.7 mmol), tert-butyl 4- (aminomefhyl)-4-methylpiperidine-l-carboxylate (160 mg, 0.7 mmol), and diisopropylethylamine (181 mg, 1.4 mmol) in DMF (3 mL). After addition, the reaction mixture was stirred at room temperature for 2 h, at which time LCMS indicated that the reaction had gone to completion. The mixture was quenched by addition of water (5 mL) and extracted with ethyl acetate (2 x 10 mL). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give the crude title compound (275 mg, 94% yield) as light brown oil. This crude material was used directly in the next step. LCMS M/Z (M+H) 402.9., 236406-22-7

236406-22-7 1-Boc-4-(Aminomethyl)-4-methylpiperidine 23282898, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); 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.885279-92-5,1-Boc-1,8-diaza-spiro[4.5]decane,as a common compound, the synthetic route is as follows.

EXAMPLE 7 N-[2-Amino-5-(2-thienyl)phenyl]-6-(1,8-diazaspiro[4.5]dec-8-yl)nicotinamide A mixture of tert-butyl [2-{[(6-chloropyridin-3-yl)carbonyl]amino}-4-(2-thienyl)phenyl]carbamate (200 mg, 0.47 mmol) and tert-butyl 1,8-diazaspiro[4.5]decane-1-carboxylate (200 mg, 0.83 mmol) in 5 mL of DMSO was treated with Et3N (0.104 mL) and stirred at 90 C. for 12 h. The reaction mixture was partitioned between EtOAc and saturated NaHCO3, the organic layer was dried (MgSO4), filtered and concentrated. Finally, the residue was dissolved in 1:1 TFA/CH2Cl2, stirred for 1 h and concentrated. Reverse-phase chromatography (10-100% MeCN/water with 0.05% TFA) followed by neutralization with EtOAc/sat’d NaHCO3 extraction and drying (MgSO4) gave the target spirocyclic compound: 1H NMR (600 MHz, DMSO-d6): delta 9.48 (s, 1 H), 8.72 (d, J=1.8, Hz, 1 H), 8.05 (dd, J=8.4, 1.8 Hz, 1 H), 7.42 (d, J=1.8 Hz, 1 H), 7.33 (d, J=5.4 Hz, 1 H), 7.26 (dd, J=8.4, 2.4 Hz, 1 H), 7.21 (d, J=3 Hz, 1 H), 7.02 (t, J=4.2 Hz, 1 H), 6.91 (d, J=9.6, 1 H), 6.77 (d, J=9.0, 1 H), 5.10 (s, 2 H), 3.80 (br m, 2 H), 3.57 (br m, 2 H), 2.96 (br m, 2 H), 1.79 (br m, 2 H), 1.58 (br m, 4 H); MS (ESI+): cal’d [M+H]+ 434.2, obs’d 434.2., 885279-92-5

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

Reference：
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3518-83-0, N-Ethyl-4-hydroxypiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-hydroxy-N-ethylpiperidine (267mg, 2.0 mmol) inTHF (5.0 mE) at RT was added NaH(60%w/w, 91 mg, 2.3 mmol) with stirring. The reaction mixturewas stirred at RT under nitrogen for 45 minutes. To the reac-tion mixture was then added 3-(4-chloro-6-methyl-2-pyrim-idinyl)-i-(3,4-dichlorophenyl)guanidine (4) (166 mg, 0.5mmol). The reaction mixture was stirred at RT for 5 hours and then heated to 90 C. for 18 hrs. The reaction mixture was cooled, poured into ice-water mixture and extracted with CH2C12 (2×25 mE). The CH2C12 layerwas washedwith waterand dried (Na2504), filtered and concentrated in vacuo toyield crude compound (200 mg, 94.8%). The crude com-pound was purified by column chromatography several times(silica, eluent, mixture ofCH2C12:MeOH:NH4OH in the ratio400: 50:2 respectively) to obtain the title compound (25) (20mg, 9%) as a solid. HPEC (254 nm): Method 3, Rt 2.89 miMS (ESI) mlz 425.3 [M+H].

3518-83-0, 3518-83-0 N-Ethyl-4-hydroxypiperidine 77056, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Curtana Pharmaceuticals, Inc.; BEATON, Graham; TUCCI, Fabio; RAVULA, Satheesh B.; WANG, Hua-Yu; (104 pag.)US2016/237069; (2016); 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.1211587-42-6,Benzyl 4-((chlorosulfonyl)methyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed N-[(1R,3r,5S)-8-azabicyclo[3.2.1]octan-3-yl]-5-ethyl-1,2- oxazole-3-carboxamide (100 mg, 0.40 mmol, 1.00 equiv), and tetrahydrofuran (5 mL). This was followed by the addition of lithium bis(trimethylsilyl)amide (1N in THF, 1.5 mL) dropwise with stirring at -70oC. To this was added benzyl 4- [(chlorosulfonyl)methyl]piperidine-1-carboxylate (200 mg, 0.60 mmol, 1.50 equiv) in several portions at -70oC. The resulting solution was stirred for 30 min at -70oC in a dry ice bath. The reaction mixture was stirred for an additional 16 h at 25oC. The resulting solution was diluted with 30 mL of ethyl acetate andwashed with 2×15 mL of H2O. The resulting mixture was concentrated under vacuum. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (2:3). This resulted in 140 mg (64%) of benzyl 4-[[(1R,3r,5S)-3-(5-ethyl-1,2-oxazole-3-amido)-8- azabicyclo[3.2.1]octane-8-sulfonyl]methyl]piperidine-1-carboxylate as white solid. LCMS (method C, ESI): RT = 1.53 min, m/z = 545.0 [M+H]+., 1211587-42-6

1211587-42-6 Benzyl 4-((chlorosulfonyl)methyl)piperidine-1-carboxylate 50988934, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; EPIZYME, INC.; MITCHELL, Lorna Helen; BELL, Andrew Simon; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (375 pag.)WO2016/40515; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem