Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.118511-81-2,1-(Piperidin-4-yl)-1H-indole,as a common compound, the synthetic route is as follows.

EXAMPLE 4 A mixture of 2-bromoethanol (3.75 g), 1-(4-piperidinyl)-1H-indole (5 g) and sodium hydrogen carbonate (4.2 g) in ethanol (100 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was stirred in water and this mixture was extracted with CH2 Cl2. The separated organic layer was dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE and the solvent was evaporated, yielding 4 g (64%) of 4-(1H-indol-1-yl)-1-piperidineethanol (intermediate 8).

118511-81-2, 118511-81-2 1-(Piperidin-4-yl)-1H-indole 14090755, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Janssen Pharmaceutica, N.V.; US5919788; (1999); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.710972-40-0,tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,710972-40-0

Step 2: To a solution of compound 21a (1 eq.) in dichloromethane, compound 11a (1.5 eq.HOAT (1.5 eq.), HATU (2 eq.), DIPEA (6 eq.), stirred at room temperature for 12 hours.The solvent is then sparged and isolated by direct column chromatography to afford intermediate 21b.

As the paragraph descriping shows that 710972-40-0 is playing an increasingly important role.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Chinese Academy Of Sciences Shanghai Life Sciences Institute; Zhang Ao; Gao Daming; Ni Jiabin; Hu Hongli; Ding Chunyong; (55 pag.)CN107814792; (2018); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.141774-61-0,tert-Butyl (piperidin-2-ylmethyl)carbamate,as a common compound, the synthetic route is as follows.

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), 2-N-Boc- aminomethyl piperidine (214 mg, 1.00 mmol) and DIEA (0.400 mL, 2.30 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (6 mL). 3 mL of the nBuOH solution was taken, to which l-(4-(4- aminophenyl)piperazin-l-yl)ethanone (142 mg, 0.65 mmol) was added. The solution was stirred at 116 0C for 20 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give tert-butyl (l-(2-(4-(4-acetylpiperazin-l-yl)phenylamino)-5-fluoropyrimidin-4- yl)piperidin-2-yl)methylcarbamate (56 mg). MS 528.4 (M+H).

141774-61-0, As the paragraph descriping shows that 141774-61-0 is playing an increasingly important role.

Reference：
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

914988-10-6, tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3-(6-phenylpyridin-3-yl)-6,7-dihydro-5H-pyrazolo[l ,5- a]pyrrolo[3,4-d]pyrimidin-8-amine (0.36 mmol), D-(-)-lactic acid (42.2 mg, 0.47 mmoL), EDC (137.8 mg, 0.72 mmol), HOBt (97.4 mg, 0.72mmol) and DIEA (376.3uL, 2.16 mraol) in DMF (3 mL) was stirred at room temperature overnight. Purification with prep-LC provided (R)-l- (8-amino-3-(6-phenylpyridin-3-yl)-5H-pyrazolo[l,5-a]pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-2- hydroxypropan-l-one: LCMS tR = 2.68 Min (10 min run, UV254nm)5 Mass calculated for, M+ 414.2, observed LC/MS m/z 415.1 (M+H)., 914988-10-6

As the paragraph descriping shows that 914988-10-6 is playing an increasingly important role.

Reference：
Patent; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla P.; SIDDIQUI, M. Arshad; WO2012/47569; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

86542-94-1,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.

Step DTo a solution of Intermediate I (1.1 g, 3.1 mmol) in EtOH (15 mL) was added l-Piperidin-4-yl-propan-1- one (437 mg, 3.1 mmol) and DIEA (1.55 g, 12 mmol). The mixture was stirred at 80 C for 3 hours then the mixture was evaporated to dryness. The crude product was purified by silica gel chromatography eluted with PE: EA =(10: 1) to give desired product (0.95 g). MS (m/e): 454 (M + H) + XH NMR (MeOD) delta, 8.55 (s, 1H), 7.65-7.74 (m, 2H), 7.56-7.63 (m, 2H), 7.46-7.54 (m, 2H), 7.42-7.44 (m, 2H), 7.36-7.38 (m, 1H), 4.50-4.80 (m, 2H), 4.23-4.60 (m, 2H),3.64-4.12 (m, 2H), 3.36-3.60 (m, 1H), 2.70-3.12 (m, 3H), 2.23-2.69 (m, 2H), 1.64-2.17 (m, mH), 1.16-1.56 (m, 1H), 0.64-1.15 (m, 3H).

86542-94-1 1-(Piperidin-4-yl)propan-1-one 18620952, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig; WANG, Jiabing; SANTARELLI, Vince; HU, Shuangxi; CUI, Mingxiang; HU, Bin; DONG, Jingchao; LUO, Yunfu; SOLL, Richard, M; WO2011/103715; (2011); 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.10338-57-5,4-(Piperidin-1-yl)benzaldehyde,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 3 in ethanol (3mL/mmol) were added an aqueous solution of potassium hydroxide (50%, 5mL/mmol) and a benzaldehyde derivative (1.0-3.5equiv.). The solution was refluxed until TLC showed complete disappearance of the starting material (2-5h). After cooling, ethanol was removed under reduced pressure, then the residue was diluted into distilled water (50mL/mmol) and an aqueous solution of hydrochloric acid (10%) was added to adjust the pH to 2-3. The mixture was then extracted with ethyl acetate or dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4, filtered off and concentrated under reduced pressure to afford the corresponding crude (Z)-2-benzylidenebenzofuran-3(2H)-one derivative., 10338-57-5

The synthetic route of 10338-57-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Meguellati, Amel; Ahmed-Belkacem, Abdelhakim; Yi, Wei; Haudecoeur, Romain; Crouillere, Marie; Brillet, Rozenn; Pawlotsky, Jean-Michel; Boumendjel, Ahcene; Peuchmaur, Marine; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 579 – 592;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

65214-86-0, 4-Diphenylmethoxypiperidine hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,65214-86-0

Example 5. Preparation of l-[4-(l,l-dimethylethyI)phenyI]-4-[4-(diphenyImethoxy)-l- piperidinyl]-l-butanone I”A mixture of 4-Benzhydryloxypiperidine hydrochloride IP’.HCl (15.19 g, 50 mmol), sodium hydrogen carbonate (10.08 g), methyl isobutyl ketone (24.30 g) and 4′-tert-butyl-4-chloro- butyrophenone III” (14.33 g) was heated to reflux (119 C) for 11 h (at this point, analysis indicated that an Ebastine solution of 81.94% purity had been formed, based on HPLC area- %). The reaction mixture was cooled to room temperature and water (100 mL) and sodium chloride (1 g) were added. The organic phase was washed with sodium chloride solution (2 x 100 mL) and oxalic acid (4.17 g) was added to the organic phase, the oxalate salt was isolated by filtration and washed twice with acetone to give the moist oxalate salt I”.H2C204 (22.06 g). The oxalate salt was suspended in water (100 mL) and aqueous ammonia (12.5 % was added dropwise until a pH of 7-7.5 was obtained). The product was isolated by filtration and washed with water (3x 20 mL). The moist product (18.97 g) was dried to give l-[4-(l,l- dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-l-piperidinyl]-l-butanone I” (13.42 g, 57.15%). HPLC 89.2 %.

65214-86-0 4-Diphenylmethoxypiperidine hydrochloride 44153518, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; AREVIPHARMA GMBH; SCHICKANEDER, Christian; MCGRATH, Matthew; SCHAeFER, Juergen; SCHUBERT, Jana; JACOB, Ulrike; MAeRTENS, Welljanne; WO2011/121099; (2011); 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.220394-97-8,1-Boc-4-(Cbz-amino)piperidine,as a common compound, the synthetic route is as follows.

(Example 1b) Benzyl N-(piperidin-4-yl)carbamate A mixture of tert-butyl 4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example 1a (13.1 g, 39.2 mmol), a 5 N aqueous hydrochloric acid solution (40 ml, 200 mmol) and methanol (40 ml) was stirred at room temperature for 23 hours. A 5 N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture under ice-cooling. Water and the solvent were distilled off from the reaction mixture while the mixture was azeotropically distilled with ethanol. Ethanol was added to the residue, the insoluble matter was removed by filtration, and the filtrate was concentrated to give the title compound (9.10 g, yield 99.1%). 1H-NMR (400 MHz, CDCl3) delta ppm; 1.31-1.42 (2H, m), 1.92-2.04 (2H, br), 2.70 (2H, d, J=12 Hz), 3.10 (2H, d, J=12 Hz), 3.56-3.68 (1H, br), 4.72-4.81 (1H, br), 5.09 (2H, s), 7.26-7.40 (5H, m).

220394-97-8, As the paragraph descriping shows that 220394-97-8 is playing an increasingly important role.

Reference：
Patent; Eisai R&D Management Co., Ltd.; YOSHIDA Ichiro; OKABE Tadashi; MATSUMOTO Yasunobu; WATANABE Nobuhisa; OHASHI Yoshiaki; ONIZAWA Yuji; HARADA Hitoshi; EP2757103; (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.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Preparation of Compound 148Step 1:(S)-tert-Butyl (l-ethyl-2-oxopiperidin-3-yl)carbamate. (S)-tert-bvAy (2-oxopiperidin- 3-yl)carbamate (1 g, 4.67 mmol) was dissolved in THF (10 mL) and the solution cooled to 0C. A 1M solution of LiHMDS (5.4 mL) in THF was added and the mixture stirred for 1 h. Iodoethane (410 iL, 5.1 mmol) was added and the reaction removed from the cooling bath and allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4C1 (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-ethyl-2-oxo-3-piperidyl]carbamate. Yield: (190 mg, 16.8%). MS: m/z (obs.) 507.0 [M+H]+. IH NMR (400 MHz, CDC13) delta 6.86 (d, J = 7.8 Hz, IH), 3.85 (s, IH), 3.30 – 3.15 (m, 5H), 1.84 (ddd, J = 26.1, 16.9, 12.3 Hz, 5H), 1.38 (s, 10H), 1.01 (t, J = 7.1 Hz, 3H).

221874-51-7, As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.

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.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

In a 1 L sealed tube, to a solution of (R)-tert-butyl (2-oxopiperidin-3-yl)carbamate (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu’- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 g Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 g). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermediate 1 (15 g, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh):? ppm 7.48 (d, J = 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08- 1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) (0145) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min., 221874-51-7

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

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHIRUDE, Pravin Sudhakar; CHATTOPADHYAY, Amit Kumar; RACHAMREDDY, Chandrasekhar; WURTZ, Nicholas R.; KICK, Ellen K.; (117 pag.)WO2018/227058; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem