Tag: M.W:200-300

62718-31-4, 1-Benzylpiperidine-4-carbonitrile is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62718-31-4, Methyl 1-benzylpiperidine-4-carboximidate dihydrochloride A solution of 20 g of 1-benzylpiperidine-4-carbonitrile in a mixture of dry dichlolomethane (200 ml) with methanol (30 ml) was cooled and saturated with a hydrogen chloride gas while maintaining the reaction system at 0 C. or below. After allowing to stand for 4 hours at 0 C., the solvent was distilled off under reduced pressure at room temperature or below and the residue was diluted with ethyl acetate. The colorless crystals thus obtained were ground, filtered and washed with ethyl acetate to thereby give 23.6 g of the title compound. 1H-NMR(CD3OD) delta ppm: 2.12(br.q, J=13.1 Hz, 2H), 2.23(br.d, J=13.1 Hz, 2H), 3.07-3.16(br.m, 1H), 3.18(br.t, J=13.1 Hz, 2H), 3.58(br.d, J=13.1 Hz, 2H), 4.18(s, 3H), 4.36(s, 2H), 7.46-7.53(m, 3H), 7.55-7.63(m, 2H)

The synthetic route of 62718-31-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Eisai Co., Ltd.; US6518423; (2003); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

62718-31-4, 1-Benzylpiperidine-4-carbonitrile is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

step E2 – A solution of 50b (5 g, 25 mmol) in THF (80 mL) was added dropwise to a solution of 3-fluoro-phenylmagnesium bromide (34 mL, 1.0 M, 34 mmol) in THF (20 mL) maintained at 0 C. The reaction mixture was stirred for 72 h and allowed to warm to RT. The reaction was quenched by the addition of saturated aqueous NH4Cl, extracted with EtOAc, dried (Na2SO4) and concentrated. EtOH (50 mL) was added and the pH was adjusted to pH 11-14 with aqueous NaOH. The mixture was heated to 60 C for 3 h, brine was added and the mixture was extracted with EtOAc. The combined organic extracts were dried (Na2SO4) and concentrated. The crude product was purified by Si?2 chromatography eluting with a gradient of DCM and DCM/MeOH/NH4OH (60/10/1) (95 to 85% DCM over 60 min) to afford 4.4 g (59%) of 52: ms (LCMS) m/z 298 (M+H)., 62718-31-4

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

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

406212-51-9, 1-tert-Butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of methyl 4-hydroxypiperidine-3-carboxylate (3.18 g, 20 mmol), aqueous sodium hydrogen carbonate (30 mL, 1M), di-tert-butyl dicarbonate (4.37 g, 20 mmol) and dichloromethane (30 mL) was stirred for 15 hours. The phases were separated and dichloromethane phase was dried over anhydrous sodium sulfate and filtrated. The filtrate was diluted to 200 mL. To the resulted solution was added imidazole (1.64 g, 24 mmol), DMAP (0.488 g, 4 mmol), and TBDMSCl (3.62 g, 24 mmol) sequentially. The reaction mixture was stirred at room temperature for 40 hours. The mixture was washed with 1N HCl solution, NaHCO3 solution and brine sequentially and dried over anhydrous sodium sulfate. Filtration and concentration gave the crude compound which was used directly in the next step. MS (m/z): 274 (M-Boc+H)+., 406212-51-9

The synthetic route of 406212-51-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); 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.108612-54-0,tert-Butyl methyl(piperidin-4-yl)carbamate,as a common compound, the synthetic route is as follows.

A solution of the above nicotinonitrile (2.4 g, 10.8 mmol) in ethanol (40 mL) was cooled in a dry ice/acetone bath. Triethylamine (1.5 mL, 11.0 mmol) and N-methyl, N-boc-4-aminopiperidine were added and the reaction mixture was allowed to warm gradually to room temperature overnight. The reaction was concentrated, taken up in ethyl acetate (200 mL) and washed with 1 N HCl (2*100 mL). The organic phase was dried (magnesium sulfate) and concentrated to provide a 4 to 1 mixture of addition products to the 6 and 2 position, respectively. These regioisomers were separated by silica gel chromatography using a gradient of ethyl acetate in hexanes as the mobile phase to provide 1.3 g (30percent) of (6′-chloro-5′-cyano-4′-difluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-methyl-carbamic acid tert-butyl ester as a white solid., 108612-54-0

The synthetic route of 108612-54-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GINN, John David; Sorcek, Ronald John; Turner, Michael Robert; Young, Erick Richard Roush; US2007/293533; (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.936130-82-4,Methyl 4-(piperidin-4-yl)benzoate hydrochloride,as a common compound, the synthetic route is as follows.,936130-82-4

Methyl 4-(piperidin-4-yl)benzoate hydrochloride (5.0 g, 17 mmol) was converted to the freebase by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford methyl 4-(piperidin-4-yl)benzoate (4.20 g, 95%) as a white solid. MS: m/z 260 (MH+).

The synthetic route of 936130-82-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

189333-49-1, 3-Benzyl-3,9-diazaspiro[5.5]undecane is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b. Preparation of final compound 5; A mixture of intermediate compound 3 (prepared according to Al.c) (0.033 mol), 3- (phenylmethyl)-3,9-diazaspiro-[5.5]-undecane (0.033 mol), Ti (iPrO)4 mol) and Pd/C (1.5 g) in thiophene (1 ml) and methanol (150 ml) was hydrogenated at 50C for 18 hours under a 5 bar pressure, then filtered over celite. Celite was washed with CH30H. The filtrate was evaporated till dryness. The residue was dissolved in CH2C12. K2C03 10 % was added. The mixture was stirred at room temperature for 30 minutes, then filtered over celite. Celite was washed with CH2C12. The filtrate was extracted with CH2C12. The organic layer was separated, dried (MgS04), filtered, and the solvent was evaporated. The residue (20 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.5; 20-45 mum). Two fractions were collected and the solvent was evaporated. The residue was dissolved in iPrOH and converted into the hydrochloric acid salt. The precipitate was filtered off and dried. Yield: 3.5 g of final compound 5 (14 %) (melting point: 183C).

189333-49-1, The synthetic route of 189333-49-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/97795; (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.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

Intermediate 11Phenylmethyl 3-{[2-({[(1 ,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-1 – piperidinecarboxylate (D11) Phenylmethyl 3-oxo-i-piperidinecarboxylate (5 g, 21.44 mmol) was dissolved in a mixture of methanol (200 ml) and acetic acid (1.227 ml, 21.44 mmol). 1 ,1- dimethylethyl (2-aminoethyl)carbamate (10.30 g, 64.3 mmol) was added and sodium triacetoxyborohydride (11.36 g, 53.6 mmol) was also added after stirring for 1 hour. The reaction mixture was allowed to stir for a further 4 hours. Sodium bicarbonate (9.00 g, 107 mmol) was added to the reaction and the resulting mixture was concentrated in vacuo. The resulting residue was redissolved using DCM and water. The mixture was basified to pH 14 using 2M NaOH and the aqueous layer was extracted with DCM. The combined organic extracts was passed through a hydrophobic frit and concentrated in vacuo. The resulting residue was purified by silica column chromatography (Biotage SP4, eluting with a gradient from 0-20% MeOH in DCM) to give the title compound as a yellow oil (7.85 g, 20.80 mmol, 97 % yield).MS ES+ve m/z 275 (M+H)1H NMR (400 MHz, DMSO-D6) delta ppm 1.2 (m, 1 H) 1.4 (m, 1 H) 1.4 (s, 9 H) 1.6 (m, 2 H) 1.8 (m, 1 H) 2.4 (m, 1 H) 2.6 (m, 2 H) 2.7 (m, 1 H) 2.9 (m, 3 H) 3.7 (m, 1 H) 3.8 (m, 1 H) 5.1 (s, 2 H) 6.7 (m, 1 H) 7.3 (m, 5 H)

As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; BESWICK, Paul, John; GLEAVE, Robert, James; WO2010/91721; (2010); 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.56839-43-1,1-(4-Ethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one hydrochloride,as a common compound, the synthetic route is as follows.

56839-43-1, Example 1 – Preparation of substantially enantiopure crystalline hydrochloride salts of eperisone[0082] Raceniic eperisone hydrochloride was separated into substantially enantiopure fractions of eperisone free base using ehiral chromatography. The isocratic supercritical fluid chromatography method used a mobile phase composed of liquid CO2 with a 5% eosolvent mixture of 50:50 methanol :isopropanol containing 2% isopropylamine. The column was a Chiralpak AD-H in a 3.0 x 25 cm format with a total mobile phase flow of 80 g/minute. Chromatography of 51.1 g of racemic eperisone hydrochloride afforded solutions of two fractions (Fraction 1 was earlier eluting; Fraction 2 was later eluting). Each solution was dried by rotary evaporation to give solids of each substantially pure enantiomer as the free base. Contaminating isopropylamine was removed from each fraction by adding acetonitrile to the solid and drying by rotary evaporation to remove the acetonitrile-isopropylamine azeotrope and acetonitrile. Each fraction consisted of white, waxy solids, which were dissolved in acetonitrile. Each acetonitrile solution was cooled with stirring in an ice bath and treated with a slowly bubbled stream of hydrochloride gas for 5 minutes. Rotary evaporation to remove acetonitrile yielded substantially pure, crystalline eperisone hydrochloride of each enantiomer as white powders. The yield of each fraction and enantiomeric purity of each fraction as determined by ehiral HPLC are shown in the following table;Analytical data were obtained on the final products: the XRPD patterns were as shown in FIGS. IA and IB, the DSC thermogram was as shown in FIG. 4, the 1H-NMR spectrum was as shown in FIGS. 7A-7G, the TGA profile was as shown in FIG. 10, and the Raman spectra were as shown in FIGS. 13A and 13B. In aeetonitrile, the solubility of the substantially enantiopure crystalline eperisone hydrochloride was determined to be greater than 11 mg/mL, calculated based on the total solvent used to give a solution. The optical rotation of substantially enantiopure eperisone hydrochloride fraction Fl was measured and the specific rotation calculated: (c 1.05, aeetonitrile). The optical rotation of substantially enantiopure eperisone hydrochloride fraction F2 was measured and the specific rotation calculated: (c 1.05, aeetonitrile).

56839-43-1 1-(4-Ethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one hydrochloride 123698, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BIONEVIA PHARMACEUTICALS, INC.; KALOFONOS, Isabel; STAHLY, G., Patrick; MARTIN-DOYLE, William; KALOFONOS, Dimitris; HANKO, Jason, A.; STULTS, Jeffrey, S.; KIPLINGER, Jeffrey, P.; WO2010/17135; (2010); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

710972-40-0, tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

710972-40-0, 133 (l-r2-(‘lH-Indazol-4-v?-4-morpholin-4-yl-thieno^3.2-dlpyrimidin-6-ylmethyll- piperidin-4-yU-(2-methoxy-ethyl)-miazol-2-ylmethyl-amine.Via [l-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)- piperidin-4-yl]-(2-methoxy-ethyl)-thiazol-2-ylmethyl-amine, prepared from (2- methoxy-ethyl)-piperidin-4-yl-thiazol-2-ylmethyl-amine.Amine preparation: 4-(2-Methoxy-ethylamino)-piperidine-l-carboxylic acid tert-butyl ester (465mg) and 2-thiazolecarboxaldehyde (19OuI) were stirred in dry 1,2-dichloroethane (5mL)for 1 h. Next were added acetic acid (1 eq.) and sodium triacetoxyborohydride (458mg). The reaction mixture was stirred at room temperature overnight, diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-[(2-methoxy-ethyl)-thiazol-2-ylmethyl-amino]-piperidine-l-carboxylic acid tert-buty ester (574mg). Treatment of this compound with HCl in DCM/MeOH and basic wash with sodium hydrogen carbonate yielded the desired amine. 1H NMR (400MHz, CDCl3) 1.62-1.73 (2H, m), 1.81-1.88 (2H, m), 2.06-2.14 (2H, m), 2.60-2.68 (IH, m), 2.88 (2H, t, J=6.4Hz), 3.02-3.08 (2H, m), 3.30 (3H, s), 3.49 (2H, t, J=6.4Hz), 3.82 (2H, s), 3.92-3.96 (4H, m), 4.10 (2H, s), 4.10-4.14 (4H, m), 7.22 (IH, d, J=3.2), 7.35 (IH, s), 7.51 (IH, t, J=8.0Hz), 7.59 (IH, d, j=8.3), 7.72 (IH, d, j=3.2), 8.29 (IH, d, J=6.6Hz), 9.03 (IH, s), 10.10 (IH, br); MS (ESI+) 605 (MH+).

710972-40-0 tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate 43652134, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; PIRAMED LIMITED; WO2006/46031; (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.180307-56-6,tert-Butyl 4-vinylpiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To the mixture of Zn (4.64 g, 70.99 mmol) in dioxane (50 mL) under N 2 atmosphere was added tert-butyl 4-vinylpiperidine-1-carboxylate (5.0 g, 23.66 mmol) at 20C. Then CCl 3COCl (6.45 g, 35.49 mmol) was added at 20C. The mixture was stirred at 20C for 12 hours. To the reaction mixture was added aq. NaHCO 3 (50 mL) at 0C. Then the mixture was extracted with EA (50 mL5) and the combine organic phase was dried over anhydrous Na 2SO 4 and concentrated. The residue was purified by column chromatography (SiO 2, PE/EA = 50/1 to 20/1). Tert-butyl 4- (2, 2-dichloro-3-oxocyclobutyl) piperidine-1-carboxylate (3.0 g) was obtained. 1H NMR (400 MHz, CDCl 3) delta ppm: 4.05 -4.21 (m, 2 H) 3.04 -3.27 (m, 2 H) 2.77 (br, 2 H) 2.60 (q, J = 10.4 Hz, 1H) 2.03 -2.10 (m, 1H) 1.84 -1.97 (m, 1H) 1.52 -1.63 (m, 1H) 1.46 (s, 9 H) 1.16 -1.41 (m, 3 H)., 180307-56-6

As the paragraph descriping shows that 180307-56-6 is playing an increasingly important role.

Reference：
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem