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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.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 103-49-1 |
Formula : | C14H15N |
M.W : | 197.28 |
SMILES Code : | C1(CNCC2=CC=CC=C2)=CC=CC=C1 |
Synonyms : |
Bisbenzylamine
|
MDL No. : | MFCD00004770 |
InChI Key : | BWLUMTFWVZZZND-UHFFFAOYSA-N |
Pubchem ID : | 7656 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H314-H411 |
Precautionary Statements: | P264-P270-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P391-P405-P501 |
Class: | 8 |
UN#: | 2735 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
In methanol; | A. Condensed ethylene oxide (7 ml, 125 mmol) was added to a mixture of dibenzylamine (19.2 ml, 100 mmol) in methanol (20 ml) cooled to 0C. After 2 hours at room temperature, the mixture was evaporated without heating above room temperature. The residue was distilled to afford the title compound, bp. 220-225C/25 mm, which solidified on standing, mp 48C. | |
at 130℃; under 3102.97 Torr; for 18h;Inert atmosphere; Autoclave; Large scale; | Dibenzylamine (7627 g) was charged to a 24-L N2-purged pressure vessel. The reactor was pressurized and vented several times with N2, then pressurized with N2 and heated to 130 C. Ethylene oxide (1880 g) was fed into the reactor at such a rate to keep the pressure below 60 psia (?4 h). Upon completing the ethylene oxide addition, the reaction mixture was stirred at 130 C for 14 h. After lowering the temperature to 60 C and releasing pressure, 45%potassium hydroxide (70 g) was added to the vessel and the reaction mixture stirred at 110 C to remove water. The temperature was increased to 130 C and butylene oxide (11,277 g) was fed into the reactor at such a rate to keep the pressure below 60 psia (~31 h). Upon completing the addition, the reaction mixture was stirred for 4 h at 130 C. The reaction mixture was cooled to room temperature and the reaction mixture neutralized with acetic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetra-(n-butyl)ammonium iodide; at 20 - 140℃; for 26h; | Preparation Example: Preparation Acetic acid 2-dibenzylamino-ethyl ester; Stepi : 0.5 gram of dibenzylamine (2.5 mmol), 0.446 gram of ethylenecarbonate (5 mmol) and 0.215 gram of tetraethylammoniumiodide (083 mmol) were mixed together at room temperature. The solid mixture was then heated at 1409C and the resulting suspension was stirred at this temperature for 26 hours. The reaction mixture was diluted with ethyl acetate and extracted with 1 OmL of a 0.5M solution of sodium hydroxide. The aqueous phase was washed with ethyl acetate and the combined organic phases were washed twice with brine. The organic phase was dried on magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (eluant: ethylacetate/hexane 1/2) to afford 0.5 gram of N, N- dibenzyl-2-aminoethanol (yield: 83%) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | 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 |
---|---|---|
50% | With indium(III) chloride; In toluene;Inert atmosphere; Reflux; | General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With indium(III) chloride; In toluene;Inert atmosphere; Reflux; | General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With indium(III) chloride; In toluene;Inert atmosphere; Reflux; | General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.1% | With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; | Under an argon stream, the aldehyde compound 12.06g (40.0mmol) represented by the following structural formula (M1) , 8.68g (44.0mmol) dibenzyl amine, 13.39g (60.0mmol) triacetoxy sodium borohydride and 100mL of tetrahydrofuran (THF) was stirred at room temperature for 2 hours. After completion of the reaction, the solution was poured into sodium carbonate 100mL 1-M inclusions, which was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure to distill the solvent, to obtain a yellow oily substance. Silica gel chromatography [eluent: toluene / cyclohexane = 1: 1 (v / v)], white crystals were recrystallized with a mixed solvent of ethyl acetate and methanol. Thereby, the diamine compound No. I-4 of the following structural formula (M2) as a colorless crystal rod is obtained. The yield was 16.05g, the yield was 83.1percent, melting point is 99.0°C to 100.0°C . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: All chemicals were purchased from Sigma Aldrich or MERCKand were used as received without further purification. Ortho-DBET: N, N-dibenzyl-o-methyl benzamide: To a solution of o-toluicacid (2.08 g, 15.3 mmol) in methylene chloride (28 mL), a catalyticamount of DMF (2 drops) was added with stirring. Freshly distilledthionyl chloride (2.3 mL, 31.0 mmol) was added to the flask, andthe resulting solution was gently refluxed for two hours. The reactionmixture was concentrated under reduced pressure to removeexcess thionyl chloride using a warm water bath (55 C). The crudeacid chloride was redissolved in methylene chloride (28 mL), anddibenzyl amine (5.88 mL, 30.6 mmol) was carefully added to theflask, dropwise, over the course of 2-3 min (Note: exothermic, producesgaseous HCl). The solution was allowed to stir at room temperatureovernight. The organic layer was washed with water (30mL) followed by 5% HCl (30 mL), 10% NaOH (30 mL), finally withbrine (30 mL), and dried with anhydrous Na2SO4. The solutionwas filtered and concentrated under reduced pressure to yield agranular, slightly yellow solid before being dissolved in a minimumamount of hot hexanes. The solution was allowed to cool, and crystalswere collected and dried to yield 1.98 g (41% overall) of thepure N, N-dibenzyl-o-toluamide. |