Day: March 24, 2022

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

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.

Preparation of acyl-chloride: A solution of 200 mg (0.571 mmol) of the compound from Example 52A in 4 mL of dichloromethane was initially treated at RT with 249 mu (2.86 mmol) of oxalyl chloride and then with a small drop of DMF.After the reaction mixture had been stirred at RT for 2.5 h, it was concentrated to dryness on a rotary evaporator.The remaining residue was dried under high vacuum and then reacted further in the next substep. Preparation of the amide: The acid chloride obtained above was dissolved in 1 ml of dichloromethane and added to a solution of 171 mg (1.14 mmol) of 3-methylpiperidine-4-one hydrochloride and 398 mu (2.28 mmol) N, N-diisopropylethylamine in 5 ml of dichloromethane dropped.The reaction mixture was stirred at RT for 2 h.After the mixture was concentrated on a rotary evaporator to dryness, the crude product (method 6) was purified by preparative HPLC.After combining the product fractions, evaporation and drying under high vacuum, 236 mg (88% d. Th., 95% purity) of the title compound.

4629-78-1, 4629-78-1 3-Methylpiperidin-4-one hydrochloride 22728864, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAERTER, MICHAEL; DELBECK, MARTINA; KALTHOF, BERND; LUSTIG, KLEMENS; LINDNER, NIELS; KAST, RAIMUND; WASNAIRE, PIERRE; SUESSMEIER, FRANK; (372 pag.)TW2016/7950; (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

0224] 1-(Piperidin-4-yl)ethanone hydrochloride(6.07 g, 21.85 mmol) obtained in Preparation Example 6-4 was dissolvedin acetonitrile (75 mL). Potassium carbonate (K2CO3) (5.83 g, 34.96 mmol) and iodoethane (CH3CH2I) (2.77 mL,28.41 mmol) were added dropwise to the resulting solution and the solution was stirred for 18 hrs. The solution wasevaporated under reduced pressure to concentrate, diluted with EtOAc, and washed with water. The washed organicsolvent was dried over anhydrous magnesium sulfate (MgSO4) to concentrate. The resulting residue was isolated andpurified by silica gel column chromatography (dimethylchloride/methanol = 10/1) to give the white title compound (5.18g, 76 %).1H NMR (400 MHz, CDCl3) delta 2.81 (m, 2H), 2.24 (s, 3H), 2.16 (m, 1H), 2.09 (m, 2H), 1.94 (m, 2H), 1.80 (m, 2H), 1.60(m, 2H), 1.48 (m, 3H).

89895-06-7 1-(Piperidin-4-yl)ethanone hydrochloride 44151897, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
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.

To a solution of 3-aminopiperidin-2-one hydrochloride (1.50 g) in methanol (10 mL) was added AMBERLYST (registered trademark) A21 (750 mg) at room temperature. The reaction mixture was stirred at room temperature overnight, theinsoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. To a solution of the residue in ethanol (20 mL) was added 4-thioxothiazolidin-2-one (1.330 g) at room temperature. The reaction mixture wasstirred at room temperature overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) . To a solution of the residue and l-[2,4- bis (trifluoromethyl) benzyl] piperidine-4-carbaldehyde (1018 mg) in 2-propanol (10 mL) was added piperidinium acetate (436 mg) at room temperature. The reaction mixture was stirred at 60°C overnight, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel columnchromatography (NH, methanol/ethyl acetate) and recrystallized from ethyl acetate/diisopropyl ether to give the titlecompound (530 mg) .? NMR (300 MHz, DMSO-d6) delta 1.38-1.59 (2H, m) , 1.68-1.91 (5H, m) , 2.01-2.27 (4H, m) , 2.69-2.84 (2H, m) , 3.17 (2H, brs) , 3.71 (2H, s), 4.43-4.55 (1H, m) , 6.89 (1H, d, J = 8.8 Hz), 7.83 (1H, brs), 7.98 (1H, s) , 8.02-8.12 (2H, m) , 9.34 (1H, brs).MS (ESI+) : [M+H]+ 535.1.

138377-80-7, 138377-80-7 3-Aminopiperidin-2-one hydrochloride 19795138, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MATSUMOTO, Shigemitsu; ONO, Koji; TOMINARI, Yusuke; KATOH, Taisuke; MIWA, Kazuhiro; HASUOKA, Atsushi; IMAMURA, Shinichi; WO2013/18929; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

180307-56-6, tert-Butyl 4-vinylpiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3-brornophenol (1.2 g, 1.0 equiv), N-Boc-4-vinyipiperidine (2.2 g, 1.5 equiv), Pd(OAc)2 (125 mg. 0.08 equiv), and P(o-toi)s (507 mg, 024 equiv) in CFI3CN- Et3N (1:1, 16 mL) was heated at 98 C for 16 h in a sealed vial. After cooling to room temperature, the volatiles were removed in vacuo. To the residue, DCM was added, washed with water, brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel with MeOH/DCM (0-5%) as an eluent to give 2.0 g (95%) of intermediate M as a yellow oil.

180307-56-6, 180307-56-6 tert-Butyl 4-vinylpiperidine-1-carboxylate 10910832, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; ATHENEX, INC.; SMOLINSKI, Michael P.; URGAONKAR, Sameer; CLEMENTS, James Lindsay; HANGAUER, David G., JR.; (149 pag.)WO2018/170225; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem