Structure of 39959-67-6
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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. : | 39959-67-6 |
Formula : | C8H10ClN |
M.W : | 155.62 |
SMILES Code : | CC(N)C1=CC=CC=C1Cl |
MDL No. : | MFCD05215230 |
InChI Key : | RJPLGQTZHLRZGX-UHFFFAOYSA-N |
Pubchem ID : | 299767 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
Specific examples. of the optically active amine (3) include optically active isomers of alpha-ethylbenzylamine, alpha-propylbenzylamine, alpha-isopropybenzylamine, alpha,4-dimethylbenzylamine, alpha,2,5-trimethylbenzylamine, alpha,2,4,6-tetramethylbenzylamine, alpha-methyl-4-isopropylbenzylamine, 2-fluoro-alpha-methylbenzylamine, 3-fluoro-alpha-methylbenzylamine, 4-fluoro-alpha-methylbenzylamine, 4-bromo-alpha-methylbenzylamine, 2-chloro-alpha-methylbenzylamine, 3-chloro-alpha-methylbenzylamine, 4-chloro-alpha-methylbenzylamine, 2,3-dichloro-alpha-methylbenzylamine, 2,4-dichloro-alpha-methylbenzylamine, 2-methoxy-alpha-methylbenzylamine, 4-methoxy-alpha-methylbenzylamine, 2-ethoxy-alpha-methylbenzylamine, 3,4-dimethoxy-alpha-methylbenzylamine, 5-fluoro-2-methoxy-alpha-methylbenzylamine, alpha,beta-diphenylethylamine, ... | ||
6.4 g of a 27% aqueous sodium hydroxide solution was added to the aqueous layer after extracted with toluene, the aqueous solution was extracted with 50 g of toluene, and the toluene was distilled off to obtain 4.1 g of 1-(2'-chlorophenyl)ethylamine. A portion of the latter was taken out and analyzed by high performance liquid column chromatography using the optically active column. | ||
Comparative Example 11 0.6 g of potassium t-butoxide was added to a mixture of 2 g of (R)-1-(2'-chlorophenyl)ethylamine used in Example 36 and 10 g of dimethyl sulfoxide at 80 C., and the mixture was continued to stir at the same temperature for 6 hours. Then, 10 g of toluene was added thereto, and the reaction mixture was washed twice with 10 g of saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the toluene was distilled off to obtain 2.1 g of brown oil. Purification by distillation afforded 1.58 g of 1-(2'-chlorophenyl)ethylamine. A portion thereof was taken out and optical isomer ratio was analyzed by high performance liquid chromatography with the optically active column. The optical isomer ratio S/R=28.4/71.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; for 15h; | Step 1 3,2 g (20.6mmol) 1-(2-chlorophenyl)ethaneamine [CAS 39959-67-6] and 52.3 g (22.6 mmol) triethylamine were given into 20 ml dichloromethane and afterwards 2.4 g (22.6 mmol) 2-chloroethylisocyanat werde added dropwise. The mixture was allowed to react 15 hours at 20C. The volatile components were evaporated to give 1-(2-chloroethyl)-3-[1-(2-chlorophenyl)ethyl]urea (log p = 2.3) that was used in step 2 without further purification |
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