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CAS No. : | 14321-27-8 | MDL No. : | MFCD00009031 |
Formula : | C9H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HVAAHUDGWQAAOJ-UHFFFAOYSA-N |
M.W : | 135.21 | Pubchem ID : | 84352 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P210-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405-P501 | UN#: | 2735 |
Hazard Statements: | H227-H314 | Packing Group: | Ⅲ |
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 phosphoric acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; | Example 44 α-[[Ethyl(phenylmethyl)amino]methyl]-4-(1H-imidazol-1-yl)-benzenemethanol phosphoric acid salt Add α-(bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol (7.80 g, 29.2 mmol) to a room temperature solution of N-ethylbenzylamine (21.7 mL, 146.0 mmol) in tetrahydrofuran (75 mL). Reflux the resultant mixture for about 5.5 days. Cool to room temperature and concentrate in vacuo. Chromatograph the resultnat residue on alumina (neutral, activity III, 500 g) using first methylene chloride then 2.5% methanol in methylene chloride as eluent. Collect the product fractions and concentrate in vacuo. The residue is dissolved in ethanol and phosphoric acid added until the pH is 2.5. Concentration in vacuo affords the title compound. NMR (D2 O/TSP): δ=1.43(t,3), 3.44(m,4), 4.49(m,2), 5.10(br s,1), 7.41-7.85(m,11), and 9.06(s,1; exchangeable with D2 O) ppm. EtOH at 1.16 and 3.65 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In 1,4-dioxane; triethylamine;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 |
---|---|---|
65.1% | With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 25℃; for 4h;Inert atmosphere; | Under an argon stream,the aldehyde compound 5.00g (16.6mmol) represented by the formula (M5) ,2.69g (18.3mmol) N-ethylbenzylamine, 5.18g (23.2mmol) of sodium triacetoxy boron hydride and 70mL of tetrahydrofuran (THF) was stirred at an internal temperature 25 for 4 hours. After 4 hours, the 50mL 1-M aqueous sodium carbonate was poured into the contents, which was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was washed with water, concentrated and subjected to silica gel column chromatography process [eluent: toluene], and the diamine compound of the formula (M6) represents Compound No. I-6 as a colorless viscous liquid. The yield was 4.56g (10.8mmol), a yield of 65.1percent. |
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