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Tropinone is an alkamine intermediate at the branch point of biosynthetic pathways leading to various tropane alkaloids.
Synonyms: NSC 118012; Tropanone
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 532-24-1 |
Formula : | C8H13NO |
M.W : | 139.19 |
SMILES Code : | CN1C2CC(=O)CC1CC2 |
Synonyms : |
NSC 118012; Tropanone
|
MDL No. : | MFCD00005549 |
InChI Key : | QQXLDOJGLXJCSE-UHFFFAOYSA-N |
Pubchem ID : | 79038 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
43% | Tropinone (10.0 g; 71.84 mmol) was dissolved in DCE (60 mL) and treated drop-wisewith 1-chloroethyl chloroformate ACE-C1 (14.5 mL; 19.11 g; 133.7 mmol). The reaction wasallowed to stir at room temperature overnight and was then diluted with Et20 (400 mL) andfiltered. The filtrate was concentrated under reduced pressure to provide the crude chloroethylcarbamate. This compound was taken in MeOH (200 mL) and stirred at room temperature for 1h, then concentrated under reduced pressure (at 55°C) to provide the crude des-methyltropinoneas the HC1 salt (tan solid, 11.4 g, 98percent yield). The crude material was recrystallized fromacetonitrile to furnish the pure product as a white crystalline solid (5 g, 43percent yield). *H NMR(400 MHz, DMSO-d6) 8 1.79 (dd, J= 15.0, 6.9 Hz, 2H), 2.09 (m, 2H), 2.40 (d, J= 16.7 Hz,2H), 3.02 (dd, J= 17.1, 4.3 Hz, 2H), 4.23 (s, 2H), 10.00 (br s, 2H)Des-methyl tropinone (5.10 g; 31.55 mmol) was dissolved in CH2CI2 (50 mL) and treated withbenzyl chloroformate (4.29 mL; 5.11 g; 29.98 mmol) DIPEA (16.48 mL; 12.23 g; 94.66 mmol)was added drop-wise (exothermic reaction). The resulting clear solution was allowed to stir atroom temperature for 30 min and was subsequently diluted with 100 mL CH2CI2. The organicphase was washed with 1 N HC1 (2 x 100 mL), dried on Na2SC>4 and concentrated to provide thecrude product (7.2 g, 88percent yield). *H NMR (400 MHz, CDC13) 8 1.71 (dd, J= 15.0, 7.2 Hz, 2H),2.12 (m, 2H), 2.38 (d, J= 15.9 Hz, 2H), 2.67 (m, 2H), 4.62 (s, 2H), 5.22 (s, 2H), 7.38 (m, 5H). | |
Reference Example 1-1; 8-azabicvclor3.2Jloctan-3-one hydrochlorideIn 1,2-dichloroethane (100 mL) was dissolved tropinone (5.00 g). To the solution was added 1-chloroethylchloroformate (4,70 mL) at 00C, followed by stirring the mixture under heating to reflux for 6 hours. Methanol (100 mL) was added to the residue at room temperature, and the mixture was stirred under heating to reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was then washed with diethyl ether to give the title compound (4.57 g) as a pale yellow solid, mass: 126(M+ 1 )+ . | ||
Tropinone (Fl) (10.0 g; 71.84 mml) was dissolved in DCE (60 mL) and treated drop- wise with 1-chloroethyl chloroformate ACE-Cl (14.5 mL; 19.11 g; 133.7 mmol). The reaction was allowed to stir at room temperature overnight and was then diluted with Et2O (400 mL) and filtered. The filtrate was concentrated under reduced pressure to provide the crude chloroethyl carbamate. This compound was taken in MeOH (200 mL) and stirred at room temperature for 1 hr, then concentrated under reduced pressure (at 55 0C) to provide the crude des- methyltropinone (F2) as the HCl salt, a tan solid. The crude material was recrystallized from acetonitrile to furnish the pure product as a white crystalline solid. 1H NMR (400 MHz, DMSO- d6) delta 1.79 (dd, J= 15.0, 6.9 Hz, 2H), 2.09 (m, 2H), 2.40 (d, J= 16.7 Hz, 2H), 3.02 (dd, J= 17.1, 4.3 Hz, 2H), 4.23 (s, 2H), 10.00 (br s, 2H) Des-methyl tropinone (F2) (5.10 g; 31.55 mmol) was dissolved in CH2Cl2 (50 mL) and treated with benzyl chloroformate (4.29 mL; 5.11 g; 29.98 mmol) DIPEA (16.48 mL; 12.23 g; 94.66 mmol) was added drop- wise (exothermic reaction). The resulting clear solution was allowed to stir at room temperature for 30 min and was subsequently diluted with 100 mL CH2Cl2. The organic phase was washed with 1 N HCl (2 x 100 mL), dried on Na2SO4 and concentrated to provide the crude product (F3). 1H NMR (400 MHz, CDCl3) delta 1.71 (dd, J= 15.0, 7.2 Hz, 2H), 2.12 (m, 2H), 2.38 (d, J= 15.9 Hz, 2H), 2.67 (m, 2H), 4.62 (s, 2H), 5.22 (s, 2H), 7.38 (m, 5H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dichloro-ethane; at 0℃; for 16h;Heating / reflux; | To a stirring solution OF TROPINONE (LOG, 72MMOL) into 350ML DCE at 0°C was added 1-chloroethyl chloroformate (11. 6ML, 108MMOL). The reaction mixture was then heated to reflux and stirred for 16 hours. Upon completion (TLC), volatiles were removed in vacuo and the dark brown residue was washed with ether and filtered. The filtrate was concentrated under reduced pressure and the product formed a brown oil (Yield: 12.65g, 54. 7MMOL). The brown oil was dissolved in 100mL MEOH and set to reflux for 2 hours. Upon completion (TLC), the methanol was removed in vacuo and the residue was dissolved in ether. Solid particulates were filtered, and the ether was removed under reduced pressure and 8-aza-bicyclo [3.2. 1] octan-3-one hydrochloride formed as a beige solid (Yield: 5. 0g, 40mmol). The product was used without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A suspension of <strong>[6971-45-5](2-methoxyphenyl)hydrazine hydrochloride</strong> (875 mg, 5.0 mmol; TCI-US), tropinone (696 mg, 5.0 mmol; Aldrich), and 4 M HCl-dioxane (2.5 mL, 10.0 mmol; Aldrich) in ethanol (10 mL) was heated to 80 0C for 16 hours. After cooling to room temperature, the reaction mixture was concentrated, basified with 5 NNaOH (aqueous), and then extracted with ethyl acetate (3x50 mL). The combined organic phase was concentrated and the residue was purified by reverse-phase HPLC [Waters XBridge RP 18 column, 5 mum, 30x100 mm, flow rate 40 mL/minute, 20-95% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-^) delta ppm 1.62 - 1.80 (m, 1 H), 1.97 (t, J=9 Hz, 1 H), 2.24 - 2.38 (m, 2 H), 2.47 (s, 3 H), 2.57 (d, J=Yl Hz, 1 H), 3.25 - 3.36 (m, 1 H), 3.65 - 3.73 (m, 1 H), 3.92 (s, 3 H), 4.34 (d, J=4 Hz, 1 H), 6.59 (d, J=8 Hz, 1 H), 6.87 - 6.95 (m, 1 H), 6.97 - 7.04 (m, 1 H); MS (DCIZNH3) m/z 243 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 100℃; for 0.166667h;Microwave irradiation; | 0.14g (1mmol) tropinone, 0.091g (1mmol) thiosemicarbazide and 0.23g (1mmol) of crude product α- bromo - (2,4-dimethylphenyl) acetophenone was dissolved in 2mL of ethanol, microwave 100 deg.C, the reaction 10min, TLC tracking, completion of the reaction, the solvent was removed under reduced pressure, the reaction mixture was 30mL of deionized water and extracted with dichloromethane (3 × 20mL), the combined organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure , was purified by flash column system to give the title compound in 72% yield, |
Tags: Tropinone | NSC 118012 | Other Aliphatic Heterocycles | Ketones | Aliphatic Cyclic Hydrocarbons | Organic Building Blocks | Heterocyclic Building Blocks | 532-24-1
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