Heterocyclic Building Blocks-piperidine

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

207852-63-9, 1-(4-Chloropiperidin-1-yl)ethanone is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 4 4-[(4-Fluorophenyl)-2-(4-methylthienyl)methylene]piperidine hydrochloride To a stirred solution of 4-(1-acetylpiperidinyl) chloride (50 g) in dichloromethane (690 ml), under a nitrogen atmosphere, at -25 C., was sequentially added powdered aluminium chloride (71 g) followed by a solution of 2-bromo-3-methylthiophene (50 g) in dichloromethane (300 ml) over 17 min. After 30 min. water (240 ml) was added dropwise to the reaction whilst allowing the reaction temperature to rise to about +20 C. After stirring for a further 30 min the inorganic components were removed by filtration through a pad of dicalite. The layers were separated, the organic layer was washed twice with water, dried (Na2SO4) and evaporated under reduced pressure. The crude product (73 g) was purified by chromatography to yield 2-(5-bromo-4-methylthienyl)4-(1-acetylpiperidine)methanone (62.2 g); mp 105-108.5 C. (dec).

207852-63-9, As the paragraph descriping shows that 207852-63-9 is playing an increasingly important role.

Reference：
Patent; Akzo Nobel N.V.; US6288085; (2001); B1;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.109384-19-2,tert-Butyl 4-hydroxypiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

The compound 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (485 mg, 2.41 mmol) and DMAP (29.4 mg,0.241 mmol) was dissolved in DCM (15 mL), and Et3N (0.67 mL, 4.82 mmol) and MsCl (0.223 mL, 2.879 mmol) were slowly added to the reaction mixture at 0 C.After the reaction mixture was stirred at room temperature for 5 hours, an aqueous solution of NaHCO3 (25 mL, 1 M) was added.The mixture was extracted with DCM (50 mL×2). The combined organic phases were washed with brine (25 mL).Dry over anhydrous Na 2 SO 4 and concentrate under reduced pressure.The crude product obtained was used directly in the next step without further purification.The compound 4-iodo-1H-pyrazole (467.5 mg, 2.41 mmol) was dissolved in dry DMF (8 mL) then EtOAc.NaH (60%, 193 mg, 4.82 mmol) was added portionwise to the reaction mixture. Raise the reaction to room temperature,After stirring the reaction for 2 hours at room temperature, a solution of the above crude product in DMF (4 mL) was added to the mixture.After the reaction mixture was stirred at 100 C for 12 hours, the reaction was quenched by the addition of aqueous NH4Cl (20 mL).The mixture was extracted with EtOAc (40 mL×2). The combined organic phases were washed with brine (25 mL).Dry over anhydrous Na 2 SO 4 and concentrate under reduced pressure.The residue was chromatographed on silica gel (EtOAc/EtOAc)Purification to give the title compound as a yellow solid(620 mg, 68%)., 109384-19-2

109384-19-2 tert-Butyl 4-hydroxypiperidine-1-carboxylate 643502, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Zhou Shiqing; (62 pag.)CN103833753; (2017); B;,
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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14813-01-5,1-Benzylpiperidin-3-ol,as a common compound, the synthetic route is as follows.

1000ml three necked flask n-Benzyl-3-hydroxypiperidine (95.6 g, 0.5 mol) was added,2-butanone 478 ml of a solution of L-CSA (69.6 g, 0.3 mol) in 290 ml of 2-butanone was stirred at room temperature for 1 hour, and the precipitated solid appeared, kept at 0 C for 2 hours, filtered, washed with 2-butanone 30 ml, (S) -1-benzyl-3-hydroxypiperidine camphorsulfonate. (Ee: 75%)(Theory: 105.9G)., 14813-01-5

As the paragraph descriping shows that 14813-01-5 is playing an increasingly important role.

Reference：
Patent; ABA Chemicals Corporation; Lin, ZhiGang; Xu, Jun; Liu, YanQin; Que, limin; Jiang, yueheng; CAI, Tong; (13 pag.)CN103864673; (2016); B;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

221874-51-7, (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

221874-51-7, Preparation of Compound 149Step 1:(S)-tert-Butyl (l-isopropyl-2-oxopiperidin-3-yl)carbamate. (5)-tert-butyl (2- oxopiperidin-3-yl)carbamate (1.21 g, 5.69 mmol) was dissolved in DMSO (12 mL). KOH (415 mg, 7.39 mmol) was added, followed by 2-iodopropane (740 mu,, 7.4 mmol) and the mixture stirred for 72 h. The reaction was quenched by addition of saturated aqueous NH4CI (8 vol) and extracted with EtOAc (2 x 4 vol). The combined extracts were washed with brine, dried, filtered and evaporated. The desired product was isolated by silica gel chromatography to afford tert-butyl N-[(3S)-l-isopropyl-2-oxo-3-piperidyl]carbamate. Yield: (430 mg, 29.5%). MS: m/z (obs.) 279.1 [M+Na . 1H NMR (400 MHz, d6- DMSO) delta 6.83 (d, J = 8.1 Hz, 1H), 4.68 – 4.52 (m, 1H), 3.88 (d, J = 6.8 Hz, 1H), 3.12 (dd, J = 13.0, 7.2 Hz, 2H), 1.98 – 1.85 (m, 1H), 1.75 (dd, J = 12.3, 6.8 Hz, 2H), 1.56 (d, J = 17.8 Hz, 1H), 1.38 (s, 11H), 1.03 (dd, J = 6.7, 2.0 Hz, 7H).

The synthetic route of 221874-51-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); 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.10338-57-5,4-(Piperidin-1-yl)benzaldehyde,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 5 or 7 in ethanol (3 mL/mmol) were added anaqueous solution of potassium hydroxide (50%, 5 mL/mmol) anda benzaldehyde derivative (8a-h, 1.5 equiv) The solution was stirredovernight until TLC showed complete disappearance of thestarting material. Ethanol was removed under reduced pressure.The residue was diluted into distilled water and acidified with anaqueous solution of hydrochloric acid (10%), then the mixturewas basified with saturated NaHCO3 solution to adjust the pH to7-8. The precipitate was filtered, washed with water and dried atroom temperature to afford the corresponding crude auronederivative as orange to dark red solid.

10338-57-5, As the paragraph descriping shows that 10338-57-5 is playing an increasingly important role.

Reference：
Article; Li, Yan; Qiang, Xiaoming; Luo, Li; Li, Yuxing; Xiao, Ganyuan; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry; vol. 24; 10; (2016); p. 2342 – 2351;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13096-31-6,5-Hydroxypiperidine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

EXAMPLE 23 1-(3-Mercaptopropanoyl)-5-Hydroxy-L-Pipecolic Acid By substituting 5-hydroxy-L-pipecolic acid for L-proline in the procedure of Example 13 and then treating the product by the Procedure A of Example 18, 1-(3-benzoylthiopropanoyl)-5-hydroxy-L-pipecolic, and 1-(3-mercaptopropanoyl)-5-hydroxy-L-pipecolic acid are obtained.

13096-31-6, The synthetic route of 13096-31-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; E. R. Squibb & Sons, Inc.; US4105776; (1978); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem