Structure of 7731-02-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 7731-02-4 |
Formula : | C10H19N |
M.W : | 153.26 |
SMILES Code : | N1(C2CCCCC2)CCCC1 |
MDL No. : | MFCD09032128 |
InChI Key : | ULBBXWVIXXPSOD-UHFFFAOYSA-N |
Pubchem ID : | 139064 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
90%Chromat. | With CuO#NiO; at 150℃; for 16.0h;Inert atmosphere; | [0044] With reference to the conditions used in Examples 9-16, 60-150 mg of catalyst D obtained in Example 4 was weighted and added into a 40 mL glass reaction tube provided with a magnetic stirring apparatus containing 5 mmol amines having different structures and 5 mmol alcohols having different structures, respectively. After sealed, the tube was purged with N2 to replace the air in the system for three times. Next, the system was heated and stirred. The temperature was raised to 80-180 C. and then kept for 6-36 hours. The reaction was then stopped and the system was cooled down to the room temperature. The catalyst was obtained from the reaction mixture by filtration. Agilent 7890A (30 m×0.25 mm×0.33 μm capillary column, hydrogen flame ionization detector) gas chromatograph was used for quantitatively analyzing the reaction mixture. The other byproducts were qualitatively analyzed with Agilent 6890/5973 Gas Chromatography-Mass Spectrometer (equipped with NIST Mass Spectral Database chemical workstation, 30 m×0.25 mm×0.33 μm capillary column). Each of the analysis results was shown in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium tetrahydridoborate; In neat (no solvent); at 25℃; for 0.08333330000000001h; | General procedure: To a mixture of aldehyde (1 mmol), amine (1.2 mmol) and SBSA (0.05 g) in CH3CN (5 mL) or under solvent-free condition was added NaBH4 (2 mmol, 72 mg), and then the reaction mixture was stirred at room temperature (25 C) with a magnetic stirrer for 10-20 min. After completion, EtOAc (10 mL) was added to the reaction mixture, and the catalyst was easily filtered; then, crude product was washed with H2O (2-10 mL) and a saturated solution of NaHCO3 and dried over anhydrous Na2SO4. After removal of the solvent, the pure product was obtained and further purified by recrystallization with a suitable solvent (ether or CHCl3). |
89% | With ammonium acetate; In benzene; for 1.5h;Reflux; | To a 50-mL round-bottomed flask containing ammonium formate (0.69 g, 11 mmol) was added piperonal (1.65 g, 11 mmol) followed by pyrrolidine (0.78 g, 11 mmol) and toluene (20 mL). The mixture was magnetically stirred and heated at reflux with continuous removal of the water formed (Dean-Stark trap). The mixture was then cooled to room temperature and the solvent was removed by rotary evaporation. The crude product was purified by distillation under reduced pressure and afforded the amine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; | N-Cyclohexylpyrrolidine was synthesized by hydrogenation of 1-pyrrolidino-1-cyclohexene (Sigma-Aldrich) per the teachings in Example 7 of U.S. Pat. No. 6,544,495 to Saleh Elomari. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; water; | (2) A mixture of <strong>[7731-02-4]1-(1-pyrrolidinyl)cyclohexane</strong> (85.4 g) and benzyl chloride (100 ml) in dioxane (400 ml) was heated under reflux for 23 hours under nitrogen. Water (100 ml) was then added and the brown oil was distilled to give (2RS)-2-phenylmethylcyclohexanone (47.1 g). bp: 115-120 C./3 mmHg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In toluene; | EXAMPLE 31 304 g of 2,4-dihydroxy-acetophenone and 142 g of pyrrolidine are stirred in 1 l of toluene. 320 g of 1-N-pyrrolidinyl-cyclohexane are then added and the mixture is stirred for 3 hours at 25 and then for a further 3 hours at the reflux temperature. After cooling, 1 kg of ice and 1 l 4 N HCl are stirred into the dark solution. After a short time 2,2-pentamethylene-7-hydroxychroman-4-one precipitates out from the organic phase and is filtered off and rinsed with water. The toluene is separated off from the filtrate and concentrated to about 400 ml, whereupon a further fraction precipitates. Total yield 339 g (73% of the theoretical yield): melting point: 170-171. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In toluene; | (c) 1-(4-Bromophenyl)-1,3a,4,5,6,7,7a-heptahydro-7a-(1-pyrrolidino)-indazole-3-carboxylic acid ethyl ester (Formula IV, R1 =4-bromophenyl, w=2) A solution of the compound of Example 52(b) (35 g) in toluene (200 ml) was cooled to 0 C. and treated with a solution of pyrrolidinocyclohexane (15.25 g) and triethylamine (12.14 g) in toluene (60 ml). The mixture was reacted at 0 C. for 1.5 hours,. then at ambient temperature for 18 hours. The mixture was poured into ice water and extracted with ethyl acetate. Drying and evaporation of the extract gave the title compound (40 g) as an oil. IR (film): 1700, 1590, 1580, 1530, 1480, 1465 (sh), 1450 (sh), 1420, 1390, 1365, 1310, 1260, 1150, 1025, 1015 (sh), 995, 935, 835 and 775 cm-1. NMR (CDCl3) δ: 1.0-2.25, 1.37, 2.61, 3.48, 4.33, 7.37, 7.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; at 20℃; for 504.0h; | N-Cyclohexylpyrrolidine was synthesized by hydrogenation of 1-pyrrolidino-1-cyclohexene (Sigma-Aldrich) per the teachings in Example 7 of U.S. Pat. No. 6,544,495 to Saleh Elomari. 1,4-bis(N-cyclohexylpyrrolidinium)butane dication was then synthesized from <strong>[7731-02-4]N-cyclohexylpyrrolidine</strong> as follows. In a 250 mL round-bottom flask, 18.84 g <strong>[7731-02-4]N-cyclohexylpyrrolidine</strong> was dissolved in 75 mL acetone. Then 11.96 g 1,4-dibromobutane was added to the solution. The resultant solution was allowed to sit at room temperature for three weeks. The acetone was then removed by rotoevaporation. The resultant residues were then dissolved in isopropanol and the solution was then intermittently refluxed for 2-3 hour periods over the course of a week. After each refluxing period, the isopropanol was removed and the residues were washed with acetone. The product diquaternary ammonium salt then precipitated as a tan solid. The tan solid was then isolated by vacuum filtration. The resultant solid was then thoroughly rinsed with isopropanol to remove any reactant or monoquaternary products. The product was subsequently rinsed with acetone and then with ethyl ether.After drying, the purity of the product salt was verified by 1H and 13C NMR. The filtrates were then combined and the refluxing of the isopropanol solutions was repeated to obtain additional product. The purified crops were then combined and ion-exchanged into the hydroxide form by dissolving the salts in water and adding a two-fold excess of AG-1-X8 hydroxide anion-exchange resin (Bio-Rad Laboratories, Inc.) and allowing the exchange to occur overnight. The resin was then removed by filtration and the resultant SDA solution was titrated to determine the hydroxide concentration. |
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