Structure of 21970-65-0
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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. : | 21970-65-0 |
Formula : | C17H19NO |
M.W : | 253.34 |
SMILES Code : | O=C(C1=CC=CC=C1)CCN(CC2=CC=CC=C2)C |
MDL No. : | MFCD17103238 |
InChI Key : | LNCWFHRJTAQGBG-UHFFFAOYSA-N |
Pubchem ID : | 79422 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* 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 |
---|---|---|
84% | With hydrogen; In ethanol; at 20℃; under 2585.81 Torr; | General procedure: Raney-nickel was added (100 mg) to a sample of aminoketone 10 (300 mg) dissolved in ethanol (15 mL), and then was stirred for 3-4 h at room temperature under hydrogen pressure (50 psi) in a Parr apparatus. When the starting material was not detected by TLC and by the IR spectrum, the catalyst was filtered off, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, using a mixture of CH2Cl2:MeOH (20:1) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium cerium (IV) nitrate; at 90℃; for 0.166667h;Microwave irradiation; | General procedure: A mixture of ketone (2.0 eq.), amine hydrochloride (1 eq.), paraformaldehyde (1 eq.), and CAN(0.05 eq.) in PEG 400 (0.8 mL) was irradiated with a microwave power of 60 watts at 90 C for 10 min.The reaction workup was performed as follows: the mixture was quenched in 2 M NaOH, thenthe solid was collected by centrifugation, dissolved in methanol or dichloromethane (depending onthe solubility of the compound), and purified using SCX cartridge, eluting with a solution of 0.3 MNH3/MeOH in dichloromethane to remove the excess ketone. Finally, the product was isolated usingsilica gel SPE cartridge, eluting with dichloromethane to remove the nonreacted amine. Then theorganic phase was evaporated to dryness. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound J was prepared as follows: present intermediate 3 was reacted with intermediate compound 3 of WO 2004/011436 in the same way as described in Example B12 of WO 2004/011436. The obtained residue (4.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2). One fraction was collected and the solvent was evaporated. Yield: 1.43 g of compound J, which is a mixture of diastereoisomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Present intermediate 3 was prepared in the same way as intermediate 14 of WO 2004/011436, i.e. according to Example A9 of WO 2004/011436, but starting from 3-chloropropiophenone. Yield: 98% of present intermediate 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In 1,4-dioxane; triethylamine; for 1h;Reflux; | General procedure: A mixture of amine 8 (500 mg) and the corresponding 3-(N,N-dimethylamino)propiophenone hydrochloride 9 (1 mmol) was dissolved in a mixture of 1,4-dioxane (5 mL) and triethylamine (TEA, 1 mL). The solution was stirred at reflux for 0.5-2 h until the starting materials were not further detected by TLC. After cooling, the solvent was removed under reduced pressure and the crude was purified by column chromatography on silica gel, using a mixture of CH2Cl2:AcOEt (5:1) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Cat-2 (0.08 mmol, 26 mg) prepared in Preparation Example 2.2 was dissolved in 2 mL of THF, BH3-DMS (0.55 mmol, 0.05 mL) was added, and the mixture was stirred for about 7 minutes. To the reaction mixture was added dropwise a solution of 3-benzyl (methyl) aminopropiophenone (0.79 mmol, 200 mg) in 0.45 ml of THF dropwise. After 2 hours of reaction at room temperature, 5 ml of methanol was added to terminate the reaction and the reaction was heated at 80 C for 20 hours. After removal of the solvent, ethyl acetate and water were added to separate the organic layer. Ethyl acetate was added to the separated aqueous layer to further extract it. The extracted organic layer was dried with Na2SO4 and filtered. The obtained filtrate was concentrated and purified by column chromatography (hexane: ethyl acetate = 3: 1) to obtain (R) -3-benzyl (methyl) amino-1-phenylpropanol as a solid (yield: 84%). |
A1145196 [5409-62-1]
3-(Benzyl(methyl)amino)-1-phenylpropanone hydrochloride
Reason: Free-salt