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CAS No. : | 50541-93-0 | MDL No. : | MFCD00006504 |
Formula : | C12H18N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YUBDLZGUSSWQSS-UHFFFAOYSA-N |
M.W : | 190.28 | Pubchem ID : | 415852 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; In ethanol; for 54h;Heating / reflux; | A mixture of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (4.34 g, 28.1 MMOL), 4-AMINO-1- benzypiperidine (6.01 g, 30.9 MMOL), and NaOAc (2.31 g, 28.1 MMOL) in absolute ethanol (20 mL) was stirred at reflux for 54 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in CH2CI2 (100 mL) and washed with water (2 x 30 mL). The organic layer was dried over anhydrous MgS04 and concentrated in vacuo to provide the product (8. 78 g) as a dark yellow solid. 1 H NMR (400 MHz, CDCI3) 5 9.21 (s, 1 H), 8.26 (dd, J = 6.0, 0. 4 Hz, 1 H), 8.20 (broad d, J = 7.1 Hz, 1 H), 7.34-7. 25 (complex m, 5 H), 6.70 (d, J = 6.0 Hz, 1 H), 3.62-3. 53 (m, 1 H), 3.55 (s, 2 H), 2. 89-2. 79 (m, 2 H), 2.30-2. 20 (m, 2 H), 2.10-2. 00 (m, 2 H), 1.76-1. 65 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In isopropyl alcohol;Heating / reflux; | A mixture of methyl 2-bromopyrazine-3-carboxylate (J. Med. Chem. , 1969, 12, 285) (2.2 g, 10.1 mmol) and 4-AMINO-1-BENZYLPIPERIDINE (2.0 g, 10.5 mmol) was refluxed in 2- propanol overnight. Thin layer chromatography (10% methanol in ethyl acetate) showed the reaction was complete. The solvent was evaporated, and the crude product dissolved in chloroform (100 mL), which was washed with saturated sodium carbonate solution (20 ML), and dried over magnesium sulfate. The title compound was obtained as a gum (3.8 g). MS 327 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | To a solution of 4-(2,3-Epoxypropoxy)-carbazole (1 g, 4.1 mmol) in THF (30 mL) cooled to 5-10 0C, was added LiClO4 (0.44 g, 4.1 mmol) and the reaction mixture was stirred for 15 minutes. 4-Amino-l-benzylpipe?dine (1.26 mL, 6.2 mmol) was added dropwise to the above reaction mixture at room temperature and stirring was continued for 12 hours. To the reaction mixture 50 mL of saturated NH4Cl was added EPO <DP n="44"/>and stirring was continued for 5 minutes, subsequently the solution was extracted with dichloromethane (100 rnL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude compound as light brown colored paste. The crude compound was purified by silica gel column chromatography, using DCM/MeOH (7:3) to afford the title compound as pale yellow colored solid (1.2 g, 65 % yield). | |
65% | Step 1: Preparation of 3-[(1-benzylpiperidin-4-yl)amino]-1-(9H-carbazol-4-yloxy)pro-pan-2-ol To a solution of 4-(2,3-Epoxypropoxy)-carbazole (1 g, 4.1 mmol) in THF (30 mL) cooled to 5-10 C., was added LiClO4 (0.44 g, 4.1 mmol) and the reaction mixture was stirred for 15 minutes. 4-amino-1-benzylpiperidine (1.26 mL, 6.2 mmol) was added dropwise to the above reaction mixture at room temperature and stirring was continued for 12 hours. To the reaction mixture 50 mL of saturated NH4Cl was added and stirring was continued for 5 minutes, subsequently the solution was extracted with dichloromethane (100 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude compound as light brown colored paste. The crude compound was purified by silica gel column chromatography, using DCM/MeOH (7:3) to afford the title compound as pale yellow colored solid (1.2 g, 65% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75%; 21% | With triethylamine; In tetrahydrofuran; ethanol; for 12.0h;Reflux; | General procedure: The <strong>[151229-84-4]2,6-dichloropyridine-3,5-dicarbonitrile</strong>s 14 [27]-15 [28] were suspended in a mixture of THF/EtOH (2:1, v:v). Then, amine 22 or 24 [41] followed by triethylamine, were added. The mixture was then heated under reflux. After cooling, the solvent was removed in vacuo and the resulting crude submitted to flash column chromatography. |
75%; 21% | With triethylamine; In tetrahydrofuran; ethanol; at 20℃; | General procedure: 2,6-Dichloro-4-phenylpyridine-3,5-dicarbonitrile 13 or <strong>[151229-84-4]2,6-dichloropyridine-3,5-dicarbonitrile</strong> 14 was suspended in a mixture of THF/EtOH (2:1, v:v). The corresponding amines 9-12, followed by triethylamine, were then added. The mixture was then heated under reflux. After cooling, the solvent was removed in vacuum and the resulting crude submitted to flash column chromatography, to give compounds 1-8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation Example 73 Synthesis of Compound 73 (0336) (0337) Hydroxybenzophenone 2, methyl chloroacetate and K2CO3 were mixed in acetone, refluxed and stirred to afford ester 3 (step a). After completion of the reaction, an aqueous NaOH solution was added thereto, followed by acidification with HCl to obtain carboxylic acid 4 (step b). Then, 4-amino-1-benzylpiperidine was added to the carboxylic acid 4, followed by conducting the reaction in the same manner as in the preparation example 12, using carbonyl diimidazole (CDI) as a condensing agent, to obtain Compound 73. (0338) 1H-NMR (600 MHz, DMSO-d6): delta 8.04 p.p.m. (d, j=8.0 Hz, 1H), 7.74 (d, J=9.1 Hz, 2H), 7.68 (d, J=7.1 Hz, 2H), 7.65 (t, j=7.6 Hz, 1H), 7.55 (t, j=5.8 Hz, 2H), 7.27-7.32 (m, 4H), 7.23 (t, J=7.1 Hz, 1H), 7.09 (d, J=9.0 Hz, 2H), 4.58 (s, 2H), 3.63 (m, 1H), 3.44 (s, 2H), 2.74 (d, J=11.7 Hz, 2H), 1.99 (t, J=11.5 Hz, 2H), 1.70 (d, J=9.8 Hz, 2H), 1.50 p.p.m. (dq, J1=3.0 Hz, J2=11.9 Hz, 2H); (0339) 13C-NMR (150 MHz, DMSO-d6): delta 194.4, 166.2, 161.5, 138.6, 137.7, 132.2, 132.0, 129.8, 129.3, 128.7, 128.5, 128.1, 126.8, 114.6, 66.9, 62.1, 51.9, 46.1, 31.4 |