Heterocyclic Building Blocks-piperidine

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.

Methyl pipecolinate hydrochloride (9.0 g, 50 mmol) was mixed with pyridine-2- carbaldehyde (5.4 g, 50 mmol) and triethylamine (5.05 g, 50 mmol) in dichloroethane (180 mL) at room temperature. Sodium triacetoxyborohydride (14.8 g, 70 mmol) was added in one portion. After the reaction mixture was stirred at room temperature for 1.5 h, saturated sodium carbonate was added. Then the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated to give 10.9 g (93.6%) of the title compound as a pale brown [OIL. LH NMR (CDC13), 6] (ppm): 8.53 (d, 1H), 7.65 (td, 1H), 7.49 (d, 1H), 7.14 (t, 1H), 3.89 (d, 1H), 3.73 (s, 3H), 3. 68 (d, 1H), 3.25 (dd, 1H), 2.97 (m, 1H), 2.25 (m, [1H),] 1.85 (m, 2H), 1.30-1. 76 (m, 4H).

32559-18-5, The synthetic route of 32559-18-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14902; (2004); A2;,
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1187173-43-8, 2,7-Diazaspiro[4.5]decan-1-one hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,7-Diazaspiro[4.5]decan-1 -one (90 mg, 0.584 mmol) was dissolved indichloromethane (10 mL) and triethylamine (0.163 ml_, 1 .167 mmol), and 3,5- dichlorobenzenesulfonyl chloride (158 mg, 0.642 mmol) was added. After stirring for 17 h the reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 7-[(3,5-dichlorophenyl)sulfonyl]-2,7-diazaspiro[4.5]decan-1 – one (130.5 mg, 0.352 mmol, 60% yield) as a white solid. 1 H NMR (400 MHz, DMSO- d6) delta ppm 1 .35 – 1 .50 (m, 2 H) 1.50 – 1 .65 (m, 1 H) 1.65 – 1 .76 (m, 1 H) 1.87 – 1 .98 (m, 1 H) 1.98 – 2.09 (m, 1 H) 2.30 (d, J=1 1 .56 Hz, 1 H) 2.33 – 2.41 (m, 1 H) 3.12 – 3.24 (m, 2 H) 3.38 (d, J=1 1.51 Hz, 1 H) 3.65 (d, J=1 1 .51 Hz, 1 H) 7.69 – 7.82 (m, 3 H) 8.04 (t, J=1.89 Hz, 1 H). MS ES+ve m/z 363 (M+H)., 1187173-43-8

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;,
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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.

1-t-Butyl-4-piperidone (47AKU-47) 1-Benzyl-4-piperidone (1.89 g, 10 mmol) was dissolved in 15 ml acetone. Methyliodide (0.90 ml, 15 mmol) was slowly added over 5 min. After 2 hrs magnetic stirring additional Methyliodide (1.8 ml, 30 mmol) was added. After 1 hr magnetic stirring 20 ml diethyl-ether was added. Crude product was collected by filtration and washed with acetone/diethylether. White crystals were dried under vacuum giving 806 mg quartenary salt. TLC (10% methanol in dichloromethane): Rf=0.7. Partly dissolved salt in 5 ml water was added to 50 C. hot mixture of t-Butylamine (120 mg, 1.6 mmol) and Potassiumcarbonate (32 mg, 0.22 mmol) in 3 ml ethanol. The resulting mixture was stirred and heated to reflux (?80 C.) for 1 hr. After cooling water (20 ml) and dichloromethane (20 ml) were added. Phases were separated and aq. phase was re-extracted with dichloromethane and ethylacetate. Combined organic phases were dried over MgSO4 and concentrated on Rotavapor (40 C.) giving 496 mg 47AKU-47. TLC (10% methanol in dichloromethane): Rf=0.3. 1H-NMR (400 MHz, CDCl3): delta=2.82 (4H, t); 2.41 (4H, t); 1.12 (9H, s). 13C-NMR (CDCl3): delta=210.2, 54.3, 46.4, 42.4, 26.6., 3612-20-2

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

Reference：
Patent; ACADIA Pharmaceuticals Inc.; ANDERSSON, Carl-Magnus A.; CROSTON, Glenn; HANSEN, Eva Louise; ULDAM, Allan Kjaersgaard; US2015/259291; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24686-78-0,1-Benzoylpiperidin-4-one,as a common compound, the synthetic route is as follows.

REFERENCE EXAMPLE 10B In the same manner as in Reference Example 2B, omega-cyano-4-isopropoxy-3-methoxyacetophenone, 1-benzoyl-4-piperidone and sulfur were reacted to yield 2-amino-6-benzoyl-3-(4-isopropoxy-3-methoxybenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine, which was then recrystallized from ethyl acetate-hexane to yield yellow prismatic crystals having a melting point of 158 to 160 C., 24686-78-0

The synthetic route of 24686-78-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Takeda Chemical Industries, Ltd.; US6046189; (2000); A;,
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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

Step 1: Treat N-benzyl-piperidone (8.00 g, 0.0423 mol) in CH2Cl2 with (CH3)3SiCN (4.82 g, 0.0486 mol) and ZnI2 (0.68 g, 0.0021 mol). Stir at 23 C for 16 h and concentrate. Add CH3OH saturated with NH3 (30 mL) and heat at 40 C. Concentrate the resulting mixture, add CH2Cl2 (200 mL), dry (MgSO4), filter and concentrate to give 11.06 g of the desired product as a yellow oil. MS (Cl/CH4): m/e 189 (M-26).

3612-20-2, 3612-20-2 1-Benzylpiperidin-4-one 19220, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; SCHERING CORPORATION; EP1032561; (2004); B1;,
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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.

Sodium borohydride (0.90 g, 23.9 mmol) was suspended in 20 mL of 1,2-dichloroethaneunder a nitrogen atmosphere and cooled in an ice water bath. Acetic acid (4.30 g,71.6 mmol) was added dropwise with an addition funnel. It was rinsed with 10 mL of 1,2-dichloroethane. The mixture was removed from the ice water bath and stirred atroom temperature for 16 h. A solution of 1-benzyl-4-piperidone (3.00 g, 15.9 mmol),aniline (2.62 g, 17.4 mmol), acetic acid (0.96 g, 15.9 mmol), and 12 mL of 1,2-dichloroethane was added dropwise with an addition funnel. It was rinsed with 10 mLof 1, 2 dichloroethane. The mixture was stirred for 24 h at room temperature. Thereaction mixture was poured over 100 mL of a 2 M aqueous sodium hydroxide solutionand extracted with chloroform (3 ? 100 mL). The combined organic extractswere dried with sodium sulfate, filtered, and the volatiles were evaporated providing4.40 grams of the reductive amination product. The residue was taken up in 120 mL1,2-dichloroethane and propionyl chloride (7.36 g, 79.5 mmol) was added with asyringe. The mixture was heated to reflux under a nitrogen atmosphere for 20 h. Thereaction mixture was allowed to cool to room temperature and the volatiles wereevaporated. The residue was taken up with 100 mL of saturated aqueous sodiumbicarbonate and 100 mL of chloroform. The organic layer was separated. The aqueouslayer was washed with chloroform (2 ? 100 mL). The combined organic extractswere dried with sodium sulfate, filtered, and the volatiles were evaporated providing5.70 g of a tan oil. The residue was dissolved in 15 mL of isopropanol and the solutionwas gently warmed. Oxalic acid (2.21 g, 17.5 mmol) in 5 mL of water was addedwith an addition funnel. It was rinsed with 2 mL of water followed by 3 mL of isopropanol.The mixture was allowed to cool to room temperature and was placed in are frigerator for 24 h.

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

Reference：
Article; Walz, Andrew J.; Hsu, Fu-Lian; Organic Preparations and Procedures International; vol. 49; 5; (2017); p. 467 – 470;,
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923565-91-7, N-(3-Fluorophenyl)piperidin-4-amine hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

923565-91-7, Description 29: Phenylmethyl (2R)-4-{[4-(2-{4-[(3-fluorophenyl)amino]-1-piperidinyl}-2-oxoethyl) phenyl]methyl}-2-methyl-1 -piperazinecarboxylate (D29). A mixture of D28 (100mg, 0.261 mmol), Lambda/-[3-(dimethylamino)propyl]-Lambda/’- ethylcarbodiimide hydrochloride (75mg, 0.392mmol), 1-hydroxybenzotriazole (53mg, 0.392mmol), triethylamine (11OuI, 0.784mmol) and D5b hydrochloride salt (60mg, 0.261 mmol) in DMF (2ml) was stirred at room temperature for 3 days. The solvent was removed in vacuo and the residue was purified by chromatography. Elution with 0-10% MeOH/DCM gave the title compound as a colourless oil (136mg). deltaH (CDCI3, 400MHz) 7.31-7.38 (5H, m), 7.28 (2H, d), 7.19 (2H, d), 7.07 (1H, t), 6.23-6.39 (3H, m), 5.13 (2H, AB), 4.52 (1 H, m), 4.27 (1H, br s), 3.88 (2H, m), 3.74 (2H, s), 3.62 (1H, br s), 3.44 (3H, m), 3.16 (2H, m), 2.88 (1H, m), 2.76 (1H, d), 2.59 (1H1 d), 1.94-2.15 (4H, m), 1.32 (1 H, m), 1.26 (3H, m), 1.08 (1H, m). MS (ES): MH+ 559.

923565-91-7 N-(3-Fluorophenyl)piperidin-4-amine hydrochloride 53487143, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; GLAXO GROUP LIMITED; WO2007/12479; (2007); A2;,
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Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887354-02-1,(3-Chlorophenyl)(piperidin-4-yl)methanone,as a common compound, the synthetic route is as follows.

887354-02-1, iii) (S)-5-[4-(3-Chloro-benzoyl)-piperidin-1-yl]-4-({5-[2-((S)-2-cyclobutylcarbamoyl- pyrrolidin-1 -yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-5-oxo- pentanoic acid; To a solution of 150 mg (S)-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo- ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester in 7 ml DMF were added 62 mul DIPEA, 95 mg HATU and 56 mg 4-(3-chlorobenzoyl)-piperidine. After stirring for 12 h saturated NaHCC>3 solution was added and the mixture loaded on a chem elut cartridge, the crude product being eluted with dichloromethane. The solution was concentrated to a volume of 1 ml and stirred in the presence of 100 mul TFA. After stirring for 4 h the solvents were removed under reduced pressure and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1 % TFA). The fractions containing the product were lyophilized to yield the pure product. Yield: 135 mg MS(ES+): m/e = 747.

887354-02-1 (3-Chlorophenyl)(piperidin-4-yl)methanone 3645096, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; SANOFIS-AVENTIS; WO2009/80226; (2009); A2;,
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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.,768-66-1

To a solution of 2,2,6,6-tetramethylpiperidine (TMP, 68 muL, 0.403 mmol) in anhydrous t-BuOMe (TBME, 1.6 mL) at -78 C, was added n-BuLi (2.2 M in hexanes, 174 muL). The solution was stirred at room temperature for 20 min and cooled down to -10 C.

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

Reference：
Article; Li, Xiaoyong; Babu, Vaddela Sudheer; Kishi, Yoshito; Tetrahedron Letters; vol. 56; 23; (2015); p. 3220 – 3224;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6258-28-2,2-(2,6-Dioxopiperidin-4-yl)acetic acid,as a common compound, the synthetic route is as follows.

6258-28-2, Example 117 (2R)-N-(4-tert-butyl-3-fluorophenyl)-2-(((2,6-dioxopiperidin-4-yl)acetyl)amino)-2-(4-(methoxymethyl)phenyl)acetamide To a solution of (R)-2-amino-N-(4-(tert-butyl)-3-fluorophenyl)-2-(4-(methoxymethyl)phenyl)acetamide (50 mg, 0.15 mmol), DIEA (0.050 mL, 0.29 mmol) and 2-(2,6-dioxopiperidin-4-yl)acetic acid (27.3 mg, 0.16 mmol) in DMF (2.0 mL) was added HATU (66.2 mg, 0.17 mmol) at room temperature, and the mixture was stirred for 2 hr. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (21.9 mg, 0.044 mmol, 30.3%) as white crystals. MS(API): Calculated 497.6, Found 498.2(M+H) 1H NMR (300 MHz,DMSO-d6) : delta1.29 (9H, s), 2.20-2.40 (5H, m), 3.27 (3H, s), 3.30 (2H,s), 4.38 (2H,s), 5.57 (1H, d, J=7.2 Hz), 7.16-7.35 (4H, m), 7.40-7.54 (3H, m), 8.75 (1H, d, J=7.2 Hz), 10.46 (1H, s), 10.71 (1H, s).

As the paragraph descriping shows that 6258-28-2 is playing an increasingly important role.

Reference：
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; FUKASE, Yoshiyuki; FUKUMOTO, Shoji; ODA, Tsuneo; TOKUHARA, Hidekazu; ISHII, Naoki; SASAKI, Yusuke; (255 pag.)EP3018123; (2016); A1;,
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