Month: March 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32559-18-5,Methyl piperidine-2-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.,32559-18-5

A solution of methyl piperidine-2-carboxylate hydrochloride (5 g, 27 mmol, Aldrich) in NH4OH (100 mL) was stirred at RT for 4 h. Then, the mixture was concentrated in vacuo to give the title compound, which was used in the next step without purification. MS (ESI, positive ion) m/z: 129 (M+1).

As the paragraph descriping shows that 32559-18-5 is playing an increasingly important role.

Reference：
Patent; Gore, Vijay Keshav; Ma, Vu Van; Norman, Mark H.; Ognyanov, Vassil I.; Xi, Ning; US2006/84640; (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.1187173-43-8,2,7-Diazaspiro[4.5]decan-1-one hydrochloride,as a common compound, the synthetic route is as follows.

1187173-43-8, 2,7-Diazaspiro[4.5]decan-1 -one hydrogen chloride (100 mg, 0.524 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.146 mL, 1 .047 mmol). Then 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride (0.098 mL, 0.577 mmol) was added and stirred for 16 h. The reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 7-({3-[(trifluoromethyl)oxy]phenyl}- sulfonyl)-2,7-diazaspiro[4.5]decan-1 -one (85 mg, 0.222 mmol, 42% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1 .32 – 1 .48 (m, 2 H) 1.50 – 1 .64 (m, 1 H) 1 .65 – 1 .75 (m, 1 H) 1.89 – 1 .98 (m, 1 H) 1.99 – 2.09 (m, 1 H) 2.18 – 2.28 (m, 2 H) 3.19 (t, J=7.10 Hz, 2 H) 3.30 – 3.37 (m, 1 H) 3.65 (d, J=1 1 .62 Hz, 1 H) 7.69 (s, 1 H) 7.73 – 7.85 (m, 4 H). MS ES+ve m/z 379 (M+H).

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

Reference：
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; GLEAVE, Robert James; HACHISU, Shuji; PAGE, Lee William; BESWICK, Paul John; WO2011/141728; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

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

Step B. Ethyl (3R)-1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}piperidine-3-carboxylate; A suspension of 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (300 mg, 0.80 mmol) in DCE (5 mL) was slowly added to a solution of ethyl (3R)-piperidine-3-carboxylate (140 mg, 0.88 mmol) and DIPEA (1.4 mL, 8.0 mmol) in DCE (25 mL). The reaction mixture was stirred overnight at ambient temperature and the solvent was concentrated. The product was purified by MPLC on silica gel using 60-90% EtOAc/Heptane to provide the title compound as white solid. Yield: 265 mg (66%); 1H NMR (400 MHz, CDCl3) delta 1.26 (t, J=7.13 Hz, 3H), 1.33 (td, J=12.55, 4.00 Hz, 1H), 1.50-1.57 (m, 3H), 1.59 (s, 9H), 1.62-1.71 (m, 2H), 1.72-1.84 (m, 1H), 1.90-2.02 (m, 1H), 2.22-2.38 (m, 2H), 2.44 (t, J=11.03 Hz, 1H), 2.57-2.69 (m, 1H), 3.28-3.41 (m, 2H), 3.70 (d, J=11.33 Hz, 1H), 3.91 (dd, J=11.43, 3.81 Hz, 1H), 4.01 (dd, J=11.23, 2.83 Hz, 2H), 4.13 (q, J=7.16 Hz, 2H), 4.25 (d, J=7.42 Hz, 2H), 7.43 (d, J=8.59 Hz, 1H), 7.64 (dd, J=8.40, 1.76 Hz, 1H), 8.18 (d, J=1.17 Hz, 1H); MS (ESI) (M+H)+=492.0.

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; ASTRAZENECA AB; US2007/244092; (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.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

Example 76 (Preparation of Compound 77) A mixture of 4-fluoro-1-naphthonitrile (200 mg) (4-methyl-4-piperidinyl) methanol (242 mg), potassium carbonate (332 mg) and dimethylsulfoxide (3.0 mL) was stirred at 100C for 3 hours. After cooling to room temperature, the reactant was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain 4-[4-(hydroxymethyl)-4-methyl-1-piperidinyl]-1-naphthonitrile (256 mg) (Compound 77). mp 136 – 137C. 1H-NMR (300 MHz, CDCl3) delta: 1.10 (3H, s), 1.48 (1H, t, J=6.0 Hz), 1.55-1.61 (2H, m), 1.90 (2H, ddd, J=13.2, 10.2 and 4.2 Hz), 3.04-3.12 (2H, m), 3.24-3.31 (2H, m), 3.53 (2H, d, J=6.0 Hz), 7.04 (1H, d, J=8.1 Hz), 7.57 (1H, ddd, J=8.1, 6.9 and 1.5 Hz), 7.65 (1H, ddd, J=8.1, 6.9 and 1.5 Hz), 7.83 (1H, d, J=8.1 Hz), 8.15-8.21 (2H, m). IR (KBr) 2216, 1574 cm-1, 297172-16-8

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

Reference：
Patent; Takeda Pharmaceutical Company Limited; EP1553074; (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.768-66-1,2,2,6,6-Tetramethylpiperidine,as a common compound, the synthetic route is as follows.

Starting from commercially available pyrrole-2-carbaldehyde 1, synthesis of L- Ala- [5- (HOCH2)-2-boroPro] (I) was achieved via nine steps in an overall yield of 17%. First, pyrrole-2-carbaldehyde 1 was deprotonated with sodium hydride in tetrahydrofuran and then reacted with di-tert-butyl dicarbonate to give N-Boc-pyrrole-2-carbaldehyde 2 (see Tietze, et al. Synthesis of N-protected 2-hydroxymethylpyrroles and transformation into acyclic oligomers. Synthesis (1996), 7: 851-857). Reduction of the carbaldehyde 2 with lithium borohydride at-10C yielded the hydroxymethyl compound 3. The hydroxylmethyl group of compound 3 was then protected with a tetrahydropyranyl group to form the THP ether 4. Total yield of the first three steps was 78%, with purification by silica gel flash chromatography at each step. The protected pyrrole was deprotonated with LiTMP (generated from n-butyl lithium and tetramethylpiperidine in THF at-78C) (see Kelly, et al. The efficient synthesis and simple resolution of a prolineboronate ester suitable for enzyme-inhibition studies. Tetrahedron (1993), 49 (5): 1009-16) and quenched with trimethyl borate, then HC1 was added to hydrolyze the dimethyl boronate to give the boronic acid 5. Without further purification, compound 5 was hydrogenated over 5% Pt/C in ethyl acetate to afford pyrrolidine-2-boronic acid 6. Crude 6 was stirred with 1. 05eq. (+) -pinanediol in ether at room temperature and then purified by silica gel flash chromatography to yield the protected 5-hydroxymethylboroPro pinanediol ester 7 in 60% yield over these three steps. Removal of the tert-butoxycarbonyl (Boc) group with 4 N HC1 in dioxane gave intermediate compound 8 in a yield of 94%. Compound 8 was coupled with N-Boc-L-Ala-OH in the presence of HATU and DIPEA, then the Boc and pinane protecting groups were deprotected with BC13 to give the target dipeptide boronate I in a 38% yield over the last two steps., 768-66-1

As the paragraph descriping shows that 768-66-1 is playing an increasingly important role.

Reference：
Patent; TRUSTEES OF TUFTS COLLEGE; WO2005/82348; (2005); 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.3612-20-2,1-Benzylpiperidin-4-one,as a common compound, the synthetic route is as follows.

To a solution of compound 29-1A (19.04 g, 211.36 mmol), t-BuOK (29.65 g, 264.20 mmol) in Toluene (250 mL) was added compound 29-1 (20 g, 105.68 mmol) at 90 C and stirred at 90 C for 2 hours. TLC (PE: EA= 2: 1, Rf= 0.7) showed compound 29-1 was consumed. The mixture was filtered, the organic layers was diluted with NH4C1 (aq) (300 mL), extracted with EA (100 mL*3) and concentrated in vacuo to afford the title compound (30 g, crude), as yellow oil. LC-MS: [M+H]+ =248.3.

3612-20-2, As the paragraph descriping shows that 3612-20-2 is playing an increasingly important role.

Reference：
Patent; NOVARTIS AG; BECKWITH, Rohan Eric John; JIANG, Hua; WANG, Ce; (0 pag.)WO2020/58913; (2020); 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.1245648-32-1,tert-Butyl 4-oxo-2-(trifluoromethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

NaBH4 (76 mg; 2 mmol; 2 eq.) was added at -10°C to a solution of 1-Boc-2- trifluoromethyl- piperidin-4-one (Small Molecules inc.) (267 mg; 1 mmol; 1 eq.) in MeOH (8 mL) and the reaction mixture was stirred at -10°C for 1 hour. Sat. aq. NH4CI (3 mL) was added and the resulting mixture was allowed to return to room temperature. The MeOH was evaporated in vacuo and the resulting aqueous layer extracted with DCM (4x). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (269 mg, 100percent) as a colourless oil. 1H NMR (CDCI3) delta 4.74 (br s, 1 H), 4.19-3.93 (m, 2H), 3.42-3.17 (m, 1H), 2.14-1.90 (m, 2H), 1.90-1.52 (m, 3H), 1.52-1.37 (m, 9H)., 1245648-32-1

1245648-32-1 tert-Butyl 4-oxo-2-(trifluoromethyl)piperidine-1-carboxylate 71607278, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; MERCK PATENT GMBH; SWINNEN, Dominique; MONTAGNE, Cyril; POMEL, Vincent; QUATTROPANI, Anna; MOLETTE, Jerome; GERBER, Patrick; WO2013/91773; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

78190-11-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78190-11-1,1-[(Benzyloxy)carbonyl]-3-piperidinecarboxylic acid,as a common compound, the synthetic route is as follows.

A mixture of 1-[(benzyloxy)carbonyl]piperidine-3-carboxylic acid (2.44 g), 3-chloro-6-hydrazinopyridazine (1.34g), WSCD hydrochloride (2.13 g) and methylene chloride (60 ml) was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant reside was combined with acetic acid (80 ml), stirred at 100C for 2 days, and then the solvent was distilled off under reduced pressure. The resultant crude crystals were washed with ethanol, and stirred with heating under reflux in piperidine (10 ml) for 3 hours. The reaction solution was concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: chloroform_methanol=97:3). The resultant colorless solids were combined with ethanol (40 ml) and 10% palladium-carbon (150 mg), and stirred under hydrogen atmosphere at room temperature for 6 hours, and then the catalyst was filtered off. The resultant filtrate was concentrated under reduced pressure to obtain 6-piperidin-1-yl-3-piperidin-3-yl-1,2,4-triazolo[4,3-b]pyridazine (1.18 g) as a colorless amorphous.

The synthetic route of 78190-11-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1481977; (2004); 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.85908-96-9,N-Boc-2-Piperidone,as a common compound, the synthetic route is as follows.

85908-96-9, Tert-butyl 2-oxopiperidine-1-carboxylate (8.22 g, 41.3 mmol) was dissolved in dry tetrahydrofuran (80 mL), then the solution was cooled to -78 C and to this was added dropwise LiHMDS (1.0 M in THF, 103 mL, 103 mmol) followed by stirring for 20 minutes followed by 3-bromoprop-1-ene (10.7 mL, 124 mmol) and the resulting reaction was stirred at this temperature for 15 minutes, then moved to room temperature and quenched with water (15 mL). The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with water (30 mL) and extracted with ethyl acetate (50 mL x 3), then the organic phases were combined. Next, the combined organic phases were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was then subjected to silica gel column chromatography (EtOAc / PE (v / v) = 1/50) to give the title compound as a yellow oil (3.95 g, 35%).

The synthetic route of 85908-96-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Hu Haiyang; Dai Weilong; Li Xiaobo; Wang Tingjin; Wu Yanjun; (93 pag.)CN104974163; (2017); B;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

141774-61-0, tert-Butyl (piperidin-2-ylmethyl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DIPEA (O.lmL, 0.560mmol) and tert-butyl (piperidin-2-ylmethyl)carbamate (59.6 mg, 0.28mmol) were added to to a stirred solution of ethyl 4-(chlorosulfonyl)-3-fluoro-l-methyl-lH-pyrrole-2-carboxylate (50 mg, 0.l90mmol) in MeCN (l.84mL, 0.035mol) and stirring was continued overnight at room temperature. Volatiles were evaporated and the residue was partitioned between sat. NH4Cl solution and EtOAc. The organic layer was separated, dried over Na2S04, evaporated under reduced pressure and purified by flash cromatography on silica gel (Petroleum ether/EtOAc) to give ethyl 4-((2-(((tert-butoxycarbonyl)amino)methyl)piperidin-l-yl)sulfonyl)-3-fluoro-l- methyl-lH-pyrrole-2-carboxylate (77.82 mg, y= 93.8%). Method 1: Rt=2.l5min. m/z=348.l8 (M- l00)+ Exact mass=447.l8. The Boc protecting group was removed by dissolving the intermediate ethyl 4-((2-(((tert-butoxycarbonyl)amino)methyl)piperidin-1-yl)sulfonyl)-3-fluoro-1-methyl-1H- pyrrole-2-carboxylate in dioxane (l.7mL) and treating with hydrogen chloride 4N in dioxane (2.8lmL,l l.25mmol) at RT for lh. Volatiles were evaporated under reduced pressure to afford D39 as HC1 salt, in about quantitative yield (66.75 mg). Method 1 : Rt= l.l8min. m/z=348.l3 (M+H)+ Exact mass=347.l8., 141774-61-0

The synthetic route of 141774-61-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; OSPEDALE SAN RAFFAELE S.R.L.; IRBM S.P.A.; PROMIDIS S.R.L.; ISTITUTO NAZIONALE DI GENETICA MOLECOLARE – INGM; DE FRANCESCO, Raffaele; DONNICI, Lorena; GUIDOTTI, Luca; IANNACONE, Matteo; DI FABIO, Romano; SUMMA, Vincenzo; PRANDI, Adolfo; RANDAZZO, Pietro; GORNATI, Davide; GRILLO, Alessandro; FERRANTE, Luca; BENCHEVA, Leda Ivanova; DE MATTEO, Marilenia; FERRARA, Marco; (238 pag.)WO2020/30781; (2020); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem