Category: piperidines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.534595-51-2,1-Boc-4-(isopropylamino)piperidine,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 4-(isopropyIamino)piperidine-carboxylate (0.25 g) (prepared using similar chemistry described in Step 1 , Example 1) in CH2Cl2 (10 ml) were added 3- trifluoromethylsulfinylchloride (1.4 mL; 0.8 M in THF solution) [J. Org. Chem. USSR (Engl. Transl.) 13: 2086-2087 (1977)], N,N-dimethyIamnopyridine (2 grains), diisopropylethylamine (0.71 mL). The resulting reaction mixture was stirred at room temperature two hours, and then diluted with ether (50 mL), washed with IN HCl (50 mL) and then 50 ml 5 % KOH. The organic phase was washed with water, dried over Na2SOi, filtered and concentrated. The residue obtained was purified by silica gel chromatography using ethyl acetate/hexane (1 :3) to afford the titled compound as a white solid (110 mg). 1H NMR (CDCl3): 7.94 (s, IH), 7.87 (d, J=7.8 Hz5 IH), 7.76 (d, J=8.0 Hz, IH), 7.66 (t, J=7.8 Hz, IH), 4.2 (b, 2H)5 3.57 (qint, J=4.6 Hz5 IH)5 3.23 (m, IH), 2.74 (b5 IH), 2.60 (b, IH), 2.15 (m5 IH)5 1.95 (m5 IH)5 1.75 (m, 1 H), 1.48 (s, 9H), 1.43 (d, J=5.6 HZ5 3H)5 1.15 (b5 3H). MS: m/e 435 (M-H )+., 534595-51-2

The synthetic route of 534595-51-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK & CO., INC.; WO2007/75524; (2007); 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: A mixture of the appropriate aromatic aldehydes 2b-d (12 mmol) and compound 1 (10 mmol, 2.15 g) dissolved in ethanol (50 ml) was added slowly to an aqueous solution of sodium hydroxide (12.8 mmol) in water (10 ml). The reaction mixture was stirred at 20-25 C for 4 h. The mixture was filtrated and the solid was washed with cold water. The product was crystallized from ethanol to give 3b-d., 10338-57-5

10338-57-5 4-(Piperidin-1-yl)benzaldehyde 291354, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Abdel-Wahab, Bakr F.; Abdel-Latif, Ehab; Mohamed, Hanan A.; Awad, Ghada E.A.; European Journal of Medicinal Chemistry; vol. 52; (2012); p. 263 – 268;,
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

Part A. Preparation of N-(benzyloxycarbonyl)-2-phenylmethyl-3-piperidone. A stirring solution of N-(benzyloxycarbonyl)-3-piperidone (1000 mg, 4.25 mmol) and pyrrolidine (454 mg, 6.38 mmol, Aldrich) in dry toluene (10 mL) in a round bottom flask fitted with a Dean-Stark trap was refluxed for 4 h. The reaction was conc. in vacuo to a orange oil. The oil was dissolved in dry acetonitrile (10 mL) and then benzyl bromide (800 mg, 4.68 mmol, Aldrich) was added. The reaction was heated to reflux for 16 h and then cooled to room temperature. The reaction was quenched by the addition of 1M HCl (50 mL) and then extracted with EtOAc (4*40 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and conc. in vacuo to an oil. The oil was purified by flash chromatography (SiO2, 7-20% EtOAc in hexanes) to yield 86 mg of the product as a white solid. MS (ESI) 324 (M+H).

61995-20-8 Benzyl 3-oxopiperidine-1-carboxylate 1514169, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Ko, Soo S.; DeLucca, George V.; Duncia, John V.; Santella, III, Joseph B.; Wacker, Dean A.; US6331545; (2001); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

10338-57-5, 4-(Piperidin-1-yl)benzaldehyde is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The synthesis of compounds 5, 14-23 and 26-31 follows a multi-component procedure described by Groebke et al.1 N-Cyclohexyl-2-(4-morpholinophenyl)imidazo[1,2-a]pyridin-3- amine 17: 0.30 g (3.1 mmol) 2-aminopyridine and 0.60 g (3.1 mmol) 4-morpholinobenzaldehyde were stirred with glacial acetic acid and 35 mL anhydrous MeOH, then 0.35 g (3.1 mmol) cyclohexyl isocyanide was added. After 18 h the reaction mixture was quenched with 5 mL 2N HCl to destroy the residual isocyanide. MeOH was removed under reduced pressure and 50 mL saturated NaHCO3 solution was added. The product was extracted with EtOAc (3 x 40 mL) and the solvent was removed under reduced pressure. The purification was completed by recrystallization from EtOAc/MeOH yielding 0.50 g (42.2%) yellow solid.

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

Reference：
Article; Hieke, Martina; Roedl, Carmen B.; Wisniewska, Joanna M.; La Buscato, Estel.; Stark, Holger; Schubert-Zsilavecz, Manfred; Steinhilber, Dieter; Hofmann, Bettina; Proschak, Ewgenij; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 1969 – 1975;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

142851-03-4, Ethyl N-Boc-piperidine-4-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 41Atert-Butyl 4-(hydrazinylcarbonyl)piperidine-1-carboxylate; 10.0 g (38.9 mmol) of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate were initially charged in 35 ml of ethanol, and 3.8 ml (3.90 g, 78 mmol) of hydrazine hydrate were added with stirring. The mixture was stirred at reflux for 9 h. The reaction mixture was cooled to RT, 1.9 ml (39 mmol) of hydrazine hydrate were added and the reaction solution was stirred at reflux for another 24 h. The solvent was concentrated, ethanol (50 ml) was added and the mixture was concentrated again. Diethyl ether (150 ml) was added, and the mixture was stirred in an ultrasonic bath for 5 min. The product was filtered off and dried. This gave 9.20 g (97% of theory) of the product.LCMS (Method 6): Rt=0.95 min. (m/z=244 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.99 (s, 1H), 4.17 (br, 2H), 3.95 (br d, 2H), 2.71 (br, 2H), 2.23 (m, 1H), 1.60 (m, 2H), 1.40 (m, 11H).

142851-03-4, As the paragraph descriping shows that 142851-03-4 is playing an increasingly important role.

Reference：
Patent; BAYER SCHERING PHARMA AKTIENGESELLESCHAFT; US2011/144131; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

914988-10-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.914988-10-6,tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

[0127] Step b: N,N-diisopropylethylamine (8 mL, 46.0 mmol) was added to a mixture of (2,6- diethylphenyl)hydrazine hydrochloride (8 g, 39.9 mmol), tert-butyl 3-cyano-4-oxopiperidine-1- carboxylate (5 g, 22.3 mmol) and EtOH (60 mL) in a 250 mL round bottom flask under magnetic stirring. The resulting mixture was stirred under reflux for 3 h. Glacial acetic acid (12 mL, 208 mmol) was added and the mixture was stirred under reflux for another 2 h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc and washed with NaOH solution (2N), brine, and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by silica gel flash chromatography (5 to 55% EtOAc in hexanes) to give tert-butyl 3-amino-2-(2,6-diethylphenyl)-6,7-dihydro-2H-pyrazolo[4,3- c]pyridine-5(4H)-carboxylate . MS: (ES) m/z calculated for C21H31 N4O2 [M + H]+ 371.2, found 371.2. Caution: Diazonium formation could be potentially dangerous, please handle with care and wear proper personal protection equipment.

914988-10-6 tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate 42609283, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LANGE, Christopher W.; LUI, Rebecca M.; MALATHONG, Viengkham; MALI, Venkat Reddy; PUNNA, Sreenivas; SINGH, Rajinder; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (284 pag.)WO2018/222598; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

6258-28-2, 2-(2,6-Dioxopiperidin-4-yl)acetic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6258-28-2

Example 14 4-{2-[4-(2-tert-Butylphenyl)piperazin-1-yl]-2-oxoethyl}piperidine-2,6-dione A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (500 mg), (2,6-dioxopiperidin-4-yl)acetic acid (311 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (403 mg), 1-hydroxy-1H-benzotriazole monohydrate (322 mg), triethylamine (0.627 mL), and N,N-dimethylformamide (5 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to purification by high performance liquid chromatography [Column: Gilson, Ltd. High throughput purification system, YMC Combiprep ODS-A, S-5 mum, 50 mm*20 mm; Gradient cycle: H2O (contains 0.1% CF3COOH)-acetonitrile (contains 0.1% CF3COOH), 90:10 (0 min)-90:10 (1 min)-10:90 (4.2 min)-10:90 (5.4 min)-90:10 (5.5 min)-90:10 (5.6 min); Flow rate: 25 mL/min; detection wavelength: UV 220 nm] to give the title compound (47 mg, 13%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 1.41 (s, 9H), 2.35-2.74 (m, 12H), 3.20-3.31 (m, 1H), 3.85-3.98 (m, 1H), 4.40-4.50 (m, 1H), 7.13-7.21 (m, 2H), 7.30-7.34 (m, 2H), 10.72 (br, 1H).

6258-28-2 2-(2,6-Dioxopiperidin-4-yl)acetic acid 234331, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Kasai, Shizuo; McGee, JR., Kevin Francis; US2012/71489; (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.914988-10-6,tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of (±)-tert-butyl 3-cyano-4-oxo-piperidine-1-carboxylate (3.00 g, 13.3 mmol, CAS 914988-10-6) in acetone (25 mL) was added potassium carbonate (3.70 g, 26.7 mmol) and iodoethane (4.17 g, 26.7 mmol). The mixture was stirred at 25 C for 16 hrs. On completion, the reaction mixture was concentrated in vacuo to give a residue. The residue was diluted with ice water (20 mL) and extracted with dichloromethane (3 × 20 mL). The combined organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the next step directly without further purification. 1H NMR (400MHz, CDCl3) delta = 3.84 – 3.71 (m, 3H), 3.57 (t, J = 5.7 Hz, 1H), 2.79 – 2.72 (m, 1H), 2.60 – 2.50 (m, 1H), 2.36 (br. s., 1H), 2.07 – 1.99 (m, 1H), 1.53 (s, 9H), 1.12 (t, J = 7.5 Hz, 3H)., 914988-10-6

914988-10-6 tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate 42609283, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; (208 pag.)WO2017/156177; (2017); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

61869-08-7, (3S,4R)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

61869-08-7, EXAMPLE 3 Preparation of paroxetine hydrochloride hemihydrate 11.58 kg of paroxetine free base was charged into a reactor containing 81.06 L of ethyl acetate and stirred for about 15 minutes at about 30 C. to form a clear solution. The reaction mass was filtered through a filtration system containing an online filter (5 micron polypropylene cloth), a 0.45 micron cartridge polypropylene filter, and a 0.2 micron cartridge polypropylene filter, and the filtration system was washed with 34.74 L of ethyl acetate. 2.895 L of 36% aqueous hydrochloric acid was added slowly to the filtrate over about 30 minutes at about 28-33 C. The reaction mass was stirred for about 1 hour, 45 minutes at about 28-30 C. It was then cooled to about 1 C. and maintained for about 1 hour, 30 minutes at about 0-2 C. The reaction mass was centrifuged and the wet cake washed with 23.16 L of chilled ethyl acetate. The wet solid was dried at 30 C. for about 1 hour, 15 minutes under a vacuum of about 690 mm Hg. The solid was further dried at about 58 C. under a vacuum of about 690 mm Hg for about 4 hours to get 10.9 kg of the paroxetine hydrochloride.; EXAMPLE 4 Purification of paroxetine hydrochloride hemihydrate 10.9 kg of the paroxetine hydrochloride obtained in Example 3 above was charged into a clean, dry reactor containing 76.3 L of acetone and the contents were heated to reflux. 4.564 L of water was added to the reaction suspension at reflux for about 60 minutes and stirred at reflux for about 20 minutes to form a clear solution. The reaction mass was cooled slowly to about 33 C. in 2 hours and then stirred for 1 hour at about 30-33 C. 32.7 L of n-heptane was charged into the reactor and stirring was continued for about 1 hour, 30 minutes. The reaction mass was cooled to about 2 C. and stirred for about 2 hours. The reaction mass was centrifuged and wet cake was washed with 6.54 L of chilled acetone. The wet solid was dried under vacuum of about 690 mm Hg at about 30 C. for about 2 hours and then at about 55-57 C. for about 4 hours. The resultant solid was milled in a micronizer (Manufacturer: Microtech Engineering company, Model: M-50) with an air pressure of 0.5 kg/cm2 at a feed rate of 7 kg/hour and then sieved through a 10 mesh sieve yielding 8.7 Kg of paroxetine hydrochloride hemihydrate with particle size distribution: D10=2.37 mum; D50=11.1 mum; and D90=30.6 mum.

61869-08-7 (3S,4R)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine 44274603, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Thippannachar, Vijayavitthal Mathad; Jayantilal, Pravinchandra Vankawala; Elati, Chandrasekhar Ravi Ram; Kolla, Naveen Kumar; Chlamala, Subrahmanyeswara Rao; US2006/264637; (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.690261-64-4,2-(Piperidin-4-yl)pyrimidine hydrochloride,as a common compound, the synthetic route is as follows.

EXAMPLE 82; The hydrochloride salt of the pyrimidyl piperidine (Intermediate 8) (67 mg, 0.34 mmol) was combined with Intermediate 4 (100 mg, 0.28 mmol), triethylamine (46 muL, 0.35 mmol), and 4 powdered molecular sieves (100 mg) in DCM. After 15 minutes at room temperature, sodium triacetoxyborohydride (240 mg, 1.13 mmol) was added and the resulting mixture was stirred for 3 days before being filtered through celite, diluted with DCM and washed with saturated sodium bicarbonate and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give a crude oil that was purified by preparative TLC (silica gel, 0.3% NH4OH/2.7% MeOH/97% DCM) to give 110 mg of a colorless oil. Resolution of the individual diastereomers was accomplished by HPLC using a ChiralPak AD column eluting with 30% isopropanol/hexanes to give 2 single diastereomers and a single mixture of the 2 other diastereomers.First peak 10 mg: ESI-MS calc. for C28H35F3N4O: 500.28; found 504 (M+H).Second peak 11 mg: ESI-MS calc. for C28H35F3N4O: 500.28; found 504 (M+H).Third peak 7.0 mg ESI-MS calc. for C28H35F3N4O: 500.28; found 504 (M+H)., 690261-64-4

As the paragraph descriping shows that 690261-64-4 is playing an increasingly important role.

Reference：
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem