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CAS No. : | 101-06-4 | MDL No. : | MFCD00020574 |
Formula : | C16H19NO | Boiling Point : | - |
Linear Structure Formula : | (C6H5CH2)2NCH2CH2OH | InChI Key : | WTTWSMJHJFNCQB-UHFFFAOYSA-N |
M.W : | 241.33 | Pubchem ID : | 22657 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
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 |
---|---|---|
With dibromo sulfoxide; In cyclohexane; N,N-dimethyl-formamide; for 15h; | To <strong>[101-06-4]N,N-dibenzyl-2-aminoethanol</strong> (80.68 g) were added cyclohexane (500 ml) and DMF (12.9 ml), and thereto was added dropwise thionyl bromide (83.4 g). The mixture was stirred for 15 hours, and to the reaction solution was added an saturated aqueous sodium hydrogen carbonate solution in an ice-bath, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (72.1 g). 1H NMR (400 MHz, CDCl3) delta 7.48-7.39 (m, 8H), 7.36-7.33 (m, 2H), 3.74 (s, 4H), 3.43 (m, 2H), 2.97 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In ethanol; for 16h;Heating / reflux; | Example 1; Dibenzylaminoethanol:; To a 250 mL round bottom flask equipped with stirbar, reflux condensor, nitrogen inlet, and septum was added potassium carbonate (56.5 g, 0.41 mol), ethanol (80 mL), and ethanolamine (9.9 mL, 0.16 mol). The stirred solution was heated to reflux and benzyl chloride (37.9 mL, 0.33 mol) was added via syringe. The resulting solution was stirred for 16 hours at reflux, allowed to cool, then poured into water (200 mL). The solution was extracted with chloroform (3x300 mL). The combined organic layers were dried with magnesium sulfate, filtered, then evaporated to dryness. Recrystallization from hexanes yielded the product as colorless crystals (32.8 g, 83 %). 1H NMR (300 MHz, CDCl3) delta 7.33 (10 H), 3.60 (4 H), 3.58 (2 H), 2.67 (2H). 13C NMR (75 MHz, CDCl3) delta 138.9, 129.2, 128.6, 127.4, 58.7, 58.4, 55.0. |
69% | With potassium carbonate; In ethanol; for 36h;Reflux; | Dibenzylamino Ethanol Benzyl chloride (278.5g, 2.2 mol), ethanol amine (60 mL, 1 mol), potassium carbonate (283.1g, 2.05mol) and ethanol (2 L) were mixed together in a 3L 3- neck flask, fitted with an overhead stirrer, a condenser and a glass plug. The apparatus was heated up to reflux for 36 hr, after which the insoluble solid was filtered through a medium frit. The filtrate was recovered and ethanol was removed by rotoary evaporation. The viscous liquid was redissolved in ether, the solid suspension removed by filtration and extracted twice against water. The ether solution was kept and the aqueous layer was extracted twice with dichloromethane (2 x 400 mL). The fraction were recombined, dried over MgSO4, stirred over carbon black for 15 min and filtered through a celite pad. Dichloromethane was removed and the solid was redissolved into a minimal amount of ether (combined volume of 300 mL with the first ether fraction, 300 mL). Hexanes ( 1700 mL) was added and the solution was heated up gently till complete dissolution of the product. The solution was then cooled down gently, placed in the fridge (+ 40C) overnight and white crystals were obtained. The recrystallization was done a second time. 166.63g, 69% yield. 1H NMR (d6-DMSO) delta 7.39-7.24 (10H), 4.42 (IH), 3.60 (4H), 3.52 (2H), 2.52 (2H). |
69% | With potassium carbonate; In ethanol; for 36h;Reflux; | Benzyl chloride (278.5 g, 2.2 mol), ethanol amine (60 mE, 1 mol), potassium carbonate (283.1 g, 2.05 mol) and ethanol (2 E) were mixed together in a 3 E 3-neck flask, fitted with an overhead stirrer, a condenser and a glass plug. The apparatus was heated up to reflux for 36 hr, after which the insoluble solid was filtered through a medium frit. The filtrate was recovered and ethanol was removed by rotary evaporation. The viscous liquid was redissolved in ether, the solid suspension removed by filtration and extracted twice against water. The ether solution was kept and the aqueous layer was extracted twice with dichioromethane (2x400 mE). The fraction were recombined, dried over MgSO4, stirred over carbon black for 15 mm and filtered through a celite pad. Dichloromethane was removed and the solid was redissolved into a minimal amount of ether (combined volume of 300 mE with the first ether fraction, 300 mE). Rexanes (1700 mE) was added and the solution was heated up gently till complete dissolution ofthe product. The solution was then cooled down gently, placed in the fridge (+4 C.) overnight and white crystals were obtained. The recrystallization was done a secondtime. 166.63 g, 69% yield. ?RNMR(d5-DMSO)oe 7.39- 7.24 (bR), 4.42 (1R), 3.60 (4R), 3.52 (2R), 2.52 (2R). |
54% | Preparation of aminoalcohol by dibenzylation: 2-Dibenzylamino-ethanol (Intermediate) [Show Image] To a vigorously stirred solution of 6.7 ml (1.12 mol, I equiv.) ethanolamine in 120 ml of (1/1) MeOH/H2O were added 7.2 g (1.8 mol, 1.6 equiv.) of sodium hydroxide and 24.6 g (1.8 mol., 1.6 eq). The suspension was refluxed for 30' before addition of 24.5 ml (2.3 mol., 2 equiv.) of benzyl chloride. The mixture was refluxed overnight before cooled to room temperature and extracted with 3x160 ml of diethyl ether. The organic solution was dried over sodium sulphate, and evaporated. The residue was distilled Kugel Rohr (100C, 1 mm Hg). Colorless oil (54%).1H NMR (400 MHz, CDCl3) delta 7.30 (m, 10H, Ph), 3.68 (s, 4H, NCH2Ph), 3.60 (t, J = 5.4 Hz, 2H, OCH2CH2N), 2.68 (t, J = 5.4 Hz, 2H, OCH2CH2N), 2.36 (Sb, 1 H, OH).LC/MS (ES+) m/z 242.1 (M+H)+ | |
54% | 31) Preparation of aminoalcohols; a. By dibenzylation:; Preparation of 2-Dibenzylamino-ethanol (Intermediate):; [Show Image] To a vigorously stirred solution of 6.7 ml (1.12 mol, 1 equiv.) ethanolamine in 120 ml of (1/1) MeOH/H2O was added 7.2 g (1.8 mol., 1.6 equiv.) of sodium hydroxide. The suspension was refluxed for 30 minutes before addition of 24.5 ml (2.3 mol., 2 equiv.) of benzyl chloride. The mixture was refluxed overnight before cooled to room temperature and extracted with 3x160 ml of diethyl ether. The organic solution was dried over sodium sulphate, and evapored. The residue was distilled by Kugel Rohr (100C, 1 mm Hg). Colorless oil (54%). 1H NMR (400 MHz, CDCl3) delta 7.30 (m, 10H, Ph), 3.68 (s, 4H, NCH2Ph), 3.60 (t, J = 5.4 Hz, 2H, OCH2CH2N), 2.68 (t, J = 5.4 Hz, 2H, OCH2CH2N), 2.36 (sb, 1 H, OH) LC/MS (ES+) m/z 242.1 (M+H)+ | |
50% | With triethylamine; In ethanol; for 12h;Reflux; | Step 1: Preparation of 2-(dibenzylamino)ethanol (Intermediate 31) To a solution of 2-aminoethanol (500 mg, 8.19 mmol) and TEA (2.74 mL,19.7 mmol) in EtOH (11 mL) was added benzyl chloride (1.90 mL, 16.4 nimol) in EtOH (2.0 mL) at room temperature. The reaction mixture was refluxed for 12 hours.After evaporation of volatiles, the residue was diluted with diethyl ether. The mixture was extracted with diluted with diethyl ether and extracted with 2 N aq. HCI. The separated aqueous layer was neutralized with Na2CO3 and extracted with diethyl ether. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound (980 mg, 50%), which was used for the nextreaction without further purification.?H-NMR (400 MHz, CDCI3): 7.36-7.15 (m, 1OH), 3.63 (s, 4H), 3.58 (t, J= 5.2 Hz, 2H), 2.67 (t, J= 5.2 Hz, 2H) * OH peak was not observed. |