Tag: M.W:100-200

5166-67-6, Ethyl N-methylpiperidine-3-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ethyl 1-methyl-3-(2′-fluorobenzyl-nipecotate To a solution of ethyl 1-methylnipecotate (10.0 g, 58.4 mmol) in dry tetrahydrofuran (350 ml) was added at -78 C. lithium bis(trimethylsilyl)amide (80.0 ml, 80.0 mmol) as a 1.0M solution in tetrahydrofuran and the resulting solution was allowed to stir at -78 C. for 3 hours. To this was added 2-fluorobenzylchloride (7.0 ml, 8.5 g, 59 mmol) and the resulting solution was allowed to warm to room temperature over 5 hours. Thin-layer chromatography showed reaction was not complete. More 2-fluorobenzylchloride (20 ml, 2.4 g, 17 mmol) was added to the reaction mixture and the resulting solution was allowed to stir overnight, ca. 18 hours. The tetrahydrofuran was removed by evaporation in vacuo and the orange residue was dissolved in ethyl acetate. The organic solution was extracted with 0.5N HCl (4*100 ml) and the aqueous acid extracts were combined and made basic with 10N NaOH. The aqueous was then extracted with ethyl acetate (5*100 ml) and the combined extracts were dried over MgSO4 and concentrated to yield 12.1 g (74.4%) of ethyl 1-methyl-3-(2′-fluoro)-benzyl-nipecotate as an orange oil. 1 H-NMR (CDCl3) delta: 7.22-7.15 (m, 1H), 7.10-6.95 (m, 3H), 4.14-4.05 (m, 2H), 3.01 (bd, 1H, J=10.3 Hz), 2.87 (s, 2H), 2.58 (bd, 1H, J=10.3 Hz), 2.24 (s, 3H), 2.04-1.95 (m, 3H), 1.69-1.60 (m, 2H), 1.30-1.22 (m, 1H), 1.16 (t, 3H, J=7.1 Hz).

5166-67-6, The synthetic route of 5166-67-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck & Co., Inc.; US5206240; (1993); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

1019351-46-2, Methyl 4-aminopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1019351-46-2

Example VI-4 : 4- [4-(3-FIuoro-phenyl)-6-((3/?)-hydroxymethyl-3,4-dihy dro- ljff-isoquinolm-l-y^-Jl^jSltriazin-l-ylaminol-piperidine-l-carboxylic acid methyl esterStep 1) 4-[4-Chloro-6-(3-fluoro-phenyl)-[ 1 ,3 ,5]triazin-2-ylamino]-piperidine- 1 – carboxylic acid methyl ester DIPEA (583 mg, 1.1 eq) and 4-amino-piperidine-l -carboxylic acid methyl ester (713 mg, 1.1 eq) were sequentially added to 2,4-Dichloro-6-(3- fluoro-phenyl)-[l,3,5]triazine (1.Og) dissolved in CH3CN (20 ml), and stirred for 3 hours. The resulting mixture was diluted with ethyl acetate, and washed successively with water and saturated NaCl. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was purified by column chromatography to obtain the title compound (657 mg).1H NMR (300 MHz, CDCl3) delta 8.22-8.03 (m, 2H), 7.50-7.22 (m, 2H), 5.63-5.58 (m, IH), 4.60-4.10 (m, 3H), 3.72 (s, 3H), 3.12-2.98 (m, 2H), 2.15- 2.04(m, 2H), 1.53-1.40 (m, 2H).

The synthetic route of 1019351-46-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMOREPACIFIC CORPORATION; CRYSTALGENOMICS, INC.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY of Yonsei University; WO2008/72850; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Diisopropylamine (3.14 inL; 22.23 mmol; 1.1 eq.) was dissolved in THF (60 mL) and cooled to -78 C. Butyl lithium (2.5 M in hexane; 8.89 mL; 22.23 mmol; 1.1 eq.) was then added and the solution was stirred for 30 minutes at -78 C. Ethyl l-benzylpiperidine-4-carboxylate (5 g; 20.21 mmol; 1 eq.) was dissolved in THF (40 mL) and added to the LDA solution at -78 C. The solution was stirred at -78 C for 30 minutes and iodomethane (1.32 mL; 21.22 mmol; 1.05 eq.) was added. The solution was slowly warmed to room temperature and stirred at room temperature for 1 hour. Water (100 mL) was then added to the reaction followed by EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated under reduced pressure to afford the product (5.0 g, 94% yield) as an oil. The product was analytically pure and used without further purification. LC/MS m/z (M+l) 262.0, Retention time 1.78 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 8 7.24-7.14 (m, 5H), 4.08 (q, J = 7.1 Hz, 2H), 3.40 (s, 2H), 2.60-2.57 (m, 2H), 2.08-2.02 (m, 4H), 1.47-1.40 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H), 1.10 (s, 3H). [0210] l-Benzyl-4-methylpiperidine-4-carboxylate (5.0 g; 19.15 mmol) was dissolved in Et20 (50 mL) and cooled to 0 C. L1AIH4 (1.0 g; 26.3 mmol) was slowly added portion-wise to the solution. After the addition was complete, the solution was slowly warmed to room temperature and stirred for 1 h. The solution was then cooled to 0 C and slowly quenched with IN NaOH (6 mL). The resultant white precipitates were filtered and washed with EtOAc (100 mL). The combined organic layers were concentrated under reduced pressure to provide the product (3.9 g, 90% yield) as an oil which was used without further purification. LC/MS m/z M+l 220.0, retention time 0.64 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 8 7.25-7.16 (m, 5H), 3.46 (s, 2H), 3.30 (d, J= 3.9 Hz, 2H), 2.51-2.46 (m, 2H), 2.26-2.20 (m, 2H), 1.52-1.45 (m, 3H), 1.30-1.25 (m, 2H), 0.87 (s, 3H). (l-benzyl-4-methylpiperidin-4-yl)methanol (3.9 g; 17.8 mmol) was dissolved in MeOH (50 mL) and NH4CO2H (12.5 g; 178.0 mmol) was added. Pd/C (10% by weight, wet; 5.5 g) was then added and the system was flushed with nitrogen and then with hydrogen. The reaction was stirred at room temperature overnight (18 h) and then filtered through a pad of Celite. The solvent was removed under high vacuum to provide a solid that was a mixture of the amino alcohol and NH4CO2H. The crude product (2.4 g as a mixture with NH4COOH) was used in the next step without further purification. LC/MS m/z (M+l) 130.0, retention time 0.35 min; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 5 3.17 (s, 2H), 3.03-2.98 (m, 2H), 2.95-2.88 (m, 2H), 1.64-1.57 (m, 2H), 1.36-1.31 (m, 2H), 0.89 (s, 3H). [0212] (4-methylpiperidin-4-yl)methanol (2.4 g, a mixture of the amino alcohol andNELtCC^H) 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 hour at room temperature, IN HC1 (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 Na2S04, filtered, and concentrated under high vacuum. The product (1.7 g, 47% yield over 2 steps) is obtained analytically pure as an oil 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). .H NMR (400 MHz, DMSC-d6) 8 4.05 (q, J= 7.1 Hz, 2H), 3.66 (dt, J = 13.6,4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, .7=5.2 Hz, 1H),3.11 (dd, .7=23.9, 3.5 Hz, 1H), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J= 7.1 Hz, 3H), 0.93 (s, 3H).[0213] To a 100 mL round bottom flask was added DCM (30 mL) and oxalyl chloride (0.88 mL; 10.13 mmol). The solution was cooled to -78 C and treated with DMSO (1.19 mL; 16.88 mmol). The solution was stirred at -78 C for 20 minutes and then treated with ethyl 4-(hydroxymethyl)-4-methylpiperidine-l-carboxylate (1.7 g; 8.44 mmol, dissolved in 10 mL of DCM). The solution was stirred for 30 minutes at -78 C and then treated with Et3N (3.53 mL; 25.32 mmol). The solution was stirred at -78 C for 20 min and then slowly warmed to room temperature and stirred at room temperature for an additional 2 h. The solution was then treated with saturated aqueous NaHCC>3 (50 mL), diluted with DCM (50 mL), and the layers were separated. The organic layer was washed with brine (50 mL), dried over Na2SC>4, filtered, and concentrated under reduced pressure to afford 1.6 g (95% yield) of the product as an oil which was used without further purification. LC/MS m/z (M+l) 200.0, retention time 2.23 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 5 9.40 (s, 1H), 4.06 (q, J= 7.1 Hz, 2H), 3.66 (dt, J…

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; WO2006/23852; (2006); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

4629-80-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4629-80-5,1,3-Dimethylpiperidin-4-one,as a common compound, the synthetic route is as follows.

EXAMPLE 14 6-chloro-3-(1,3-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 0.97 gm (6.4 mMol) 6-chloro-1H-indole and 1.6 gm (13.0 mMol) 1,3-dimethyl-4-piperidone, 1.05 gm (63%) of the title compound were recovered as a crystalline solid. m.p.= 170-172C MS(FD): m/e=260 (M+) EA: Calculated for: C15H17N2Cl: Theory: C, 69.09; H, 6.57; N, 10.74. Found: C, 69.39; H, 6.40; N, 10.97.

As the paragraph descriping shows that 4629-80-5 is playing an increasingly important role.

Reference：
Patent; ELI LILLY AND COMPANY; EP812826; (1997); 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

Add 20 mg of calcium hydride as a desiccant to a dry 10 ml reaction tube. Nitrogen is introduced to create an oxygen-free environment for the reaction system. Take 1-ethylpiperidin-4-ol (154 mg, 1.2 mmol), Alizarin yellow R (5 mol%) was dissolved in 1.5 ml of acetonitrile and syringe was inserted into the reaction tube. After stirring for 20 minutes, 2-naphthalenesulfonyl chloride (227 mg, 1.0 mmol) was dissolved in 1.5 ml of acetonitrile and injected into the reaction system with a syringe. The reaction was carried out under a normal temperature of 30 W for 24 hours. The organic layer was extracted with ethyl acetate (20 mL×3×). The solvent was evaporated under reduced pressure, and the product was obtained by flash column chromatography to afford 232 mg (yield: 80%).

3518-83-0, As the paragraph descriping shows that 3518-83-0 is playing an increasingly important role.

Reference：
Patent; Northwest Normal University; Fu Ying; Shi Chunzhao; Xu Qinshan; (8 pag.)CN110204465; (2019); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of ammonium chloride (1.73 g, 32.3 mmol) in water (20 ml) is added a 30% ammonia solution (2 ml) followed by 1-benzyl-4-piperidone. After 20 minutes sodium cyanide (1.47 g, 30 mmol) is added portionwise over 15 minutes. After stirring for one hour, water (50 ml) is added and the products are extracted with DCM (3*50 ml), dried (MgSO4) filtered and concentrated in vacuo. Purification by chromatography on silica eluding with 50-100% EtOAc in iso-hexane affords 4-Aminomethyl-1-benzyl-piperidine-4-ylamine; [M+H]+ 216, 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Novartis AG; US2010/130506; (2010); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

89895-06-7,89895-06-7, 1-(Piperidin-4-yl)ethanone hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 65 5-chloro-2-(piperidin-4-yl)-1H-indole A mixture of 0.60 gm (3.4 mMol) 4-chlorophenylhydrazine hydrochloride and 0.54 mL (6.7 mMol) pyridine in 20 mL ethanol were stirred at 60C for 15 minutes. To this mixture was then added 4-acetylpiperidine hydrochloride and the reaction mixture was stirred for 2 hours at 70C. The reaction mixture was concentrated under reduced pressure and the residue was treated with polyphosphoric acid. This mixture was heated at 90-100C for 48 hours. The reaction mixture was quenched with a slurry of ice in 5N sodium hydroxide. The aqueous mixture was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluding with a dichloromethane gradient containing 4-20% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.26 gm (36%) of the title compound as a tan solid. MS(FD): m/e=234 (M+) EA: Calculated for: C13H15N2Cl: Theory: C, 66.52; H, 6.44; N, 11.93. Found: C, 66.24; H, 6.34; N, 11.73.

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

Reference：
Patent; ELI LILLY AND COMPANY; EP812826; (1997); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

948894-26-6,948894-26-6, 4-Methylpiperidine-4-carbonitrile hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A) ethyl 3-bromo-5-(4-cyano-4-methylpiperidin-1-yl)-1-methyl-1H-pyrazole-4-carboxylate (1113) A mixture of ethyl 3,5-dibromo-1-methyl-1H-pyrazole-4-carboxylate (2.12 g) obtained in Reference Example 2, 4-methylpiperidine-4-carbonitrile hydrochloride (1.31 g), potassium carbonate (2.82 g) and N-methyl-pyrrolidone (10 mL) was heated under a nitrogen atmosphere at 160C for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.46 g). MS (ESI+): [M+H]+ 354.9.

948894-26-6 4-Methylpiperidine-4-carbonitrile hydrochloride 57516610, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

53617-36-0, 1-Methyl-4-(piperidin-4-yl)piperazine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53617-36-0, 5f) (R)-1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate A solution of 35 mg (0.07 mmol) (R)-1-carboxy-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 25 mg (0.08 mmol) TBTU, 11 muL (0.08 mmol) triethylamine and 14 mg (0.08 mmol) 1-methyl-4-piperidin-4-yl-piperazine in 1 mL DMF was stirred overnight at RT. The reaction mixture was purified by HPLC, the fractions containing the product were combined and lyophilised. Yield: 30 mg (64percent of theory) ESI-MS: (M+H)+=661 retention time (HPLC): 5.4 min (method A)

As the paragraph descriping shows that 53617-36-0 is playing an increasingly important role.

Reference：
Patent; Boehringer Ingelheim International GmbH; US2005/256099; (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.86542-94-1,1-(Piperidin-4-yl)propan-1-one,as a common compound, the synthetic route is as follows.

86542-94-1, Preparation ofl-(l-(4-( trifluoromethoxy )benzyl )piperidin-4-yl)propan-l -one 4v[00227] 4-Trifluoromethoxy benzyl bromide (1.52g, 5.94 mmol) was first added to a solution of l-(piperidin-4-yl)propan-l-one (0.7g, 4.95 mmol) in DMF (20mL) followed by K2C03 (1.4g, 9.9 mmol) and heated overnight at 120C. The DMF was removed under vacuum and the crude mixture was partitioned between water (10 mL) in EtOAc (30 mL). The organic layer was washed with brine and concentrated. Purification by flash column chromatography afforded the desired product. (Colorless oil, 50%); 1H NMR (400MHz, CDC13), deltaEta 7.33 (d, 2H, J = 8.3 Hz, Ar), 7.15 (d, 2H, J = 8.3 Hz, Ar), 3.48 (s, 2H, NCH2Ar), 2.88 (dd, 2H, J = 8.6 Hz, 3.1 Hz, CH2), 2.47 (q, 2H, J = 7.3 Hz, CH2CO), 2.32 (tt, 1H, J = 11.4 Hz, 3.9 Hz, CH), 2.09-1.96 (m, 2H, CH2), 1.80 (d, 2H, J = 11.3 Hz, CH2), 1.74-1.62 (m, 2H, CH2), 1.04 (t, 3H, J = 7.3 Hz, CH3); MS (ES+), [M + H] + (100), 316.2, HRMS calculated for 316.1524 Ci6H2iN02F3, found 316.1525.

The synthetic route of 86542-94-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; LIVERPOOL SCHOOL OF TROPICAL MEDICINE; O’NEILL, Paul; BIAGINI, Giancarlo; WARD, Stephen A.; BERRY, Neil Graham; NIXON, Gemma; AMEWU, Richard K.; PIDATHALA, Chandrakala; HONG, Weiqian David; GIBBONS, Peter; LEUNG, Suet Ching; PACOREL, Benedicte; SHARMA, Raman; LAWRENSON, Alexandre S.; SHONE, Alison E.; SRIVASTAVA, Abhishek; WARMAN, Ashley J.; WO2012/69856; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem