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CAS No. : | 66389-80-8 | MDL No. : | MFCD08436197 |
Formula : | C13H16N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NCGBJBDHEYDWEC-UHFFFAOYSA-N |
M.W : | 232.28 | Pubchem ID : | 10799583 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
93% | With triethylamine In dichloromethane at 20℃; | To a round-bottom flask equipped with a stir bar was added 17a-b (1.0 eq), Boc2O (1.1 eq), CH2Cl2 (10mL/mmol), and triethylamine (1.5 eq). The reaction mixture was stirred at room temperature overnight. The reaction was concentrated in vacuo and partitioned between ethyl ether and 1M HCl. The organic layer were separated, washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo to give a white crystalline solid. 4.2.4.2 128 tert-Butyl (4-cyanobenzyl)carbamate (18a) Yield: 93percent. MP: 114–116°C. 1H NMR (400MHz, CDCl3) δ 7.62 (d, J=7.9Hz, 2H, -ArH), 7.39 (d, J=8.5Hz, 2H, -ArH), 4.96 (s, 1H, -NH-), 4.37 (d, J=5.9Hz, 2H, -CH2-), 1.46 (s, 9H, -CH3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | Stage #1: With triethylamine In dichloromethane at 20℃; for 0.166667 h; Stage #2: at 20℃; for 5 h; |
Triethylamine (4.932 mL, 35.583 mmol) was added to solution of 4-(aminomethyl)benzonitrile hydrochloride (5.000 g, 29.652 mmol) in dichloromethane (20 mL) at the room temperature, and the mixture was stirred for 10 mm at the same temperature. The reaction mixture was treated at the same temperature with Di-tert-butyl dicarbonate (6.795 g, 31.135 mmol) and stuffed for additional 5 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The title compound was used without further purification (tert-butyl (4-cyanobenzyl)carbamate, 6.850 g, 99.5 percent, whtie solid). |
95% | With triethylamine In dichloromethane at 0 - 20℃; for 16 h; | 4-(Aminomethyl)benzonitrile hydrochloride 1 (2.82 g, 16.7 mmol) and triethylamine (4.7 mL, 33.7 mmol) were dissolved in anhydrous CH2C12 (50 mL) at 0 °C. To this stirred solution was added di-tert-butyl dicarbonate (4.38 g, 20.1 mmol), and the reaction allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was evaporated in vacuo, and the residue was redissolved in diethyl ether (50 mL), which was washed successively with 0.5 M aq. HC1 (2 x 25 mL), saturated NaHCO3 (2 x 25 mL) and brine (25 mL). The organic layer was dried with Mg504, filtered and evaporated in vacuo to give an off-white solid. The residue was purified by flash column chromatography (Hexanes/EtOAc = 10/1) to afford tert-butyl (4- cyanobenzyl) carbamate 2 (3.69 g, yield 95 percent) as a colorless solid. It was further characterized according to the literature procedure (4). Figures ]3A-]3B show ‘H-NMR and ‘3C-NMR spectra, respectively. |
94% | With sodium carbonate In dichloromethane at 0 - 20℃; | (1) To a solution of 4-aminomethylbenzonitrile hydrochloride (n-1) (5.00 g, 29.7 mmol) in dichloromethane(167 mL), sodium carbonate (7.54 g, 71.2 mmol) was added. The reaction mixture was cooled to 0° C. and di-tert-butyl dicarbonate (7.57 mL, 32.6 mmol) was added; the resulting mixture was brought to room temperature at which it was stirred overnight. To the reaction mixture, water was added and extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure and the residue was purified by silica gel (NH) column chromatography (n-hexane:ethyl acetate=1:1) to give tert-butyl 4-cyanobenzylcarbamate (n-2) (amount, 6.48 g; yield, 94percent). |
94% | With sodium carbonate In dichloromethane at 0 - 20℃; | To a solution of 4-aminomethylbenzonitrile hydrochloride (n-1) (5.00 g, 29.7 mmol) in dichloromethane(167 mL), sodium carbonate (7.54 g, 71.2 mmol) was added. The reaction mixture was cooled to 0°C and di-tert-butyl dicarbonate (7.57 mL, 32.6 mmol) was added; the resulting mixture was brought to room temperature at which it was stirred overnight. To the reaction mixture, water was added and extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure and the residue was purified by silica gel (NH) column chromatography (n-hexane:ethyl acetate = 1:1) to give tert-butyl 4-cyanobenzylcarbamate (n-2) (amount, 6.48 g; yield, 94percent). |
80% | With sodium hydroxide In water for 16 h; | Intermediate 28: tert-butyl {4-[amino(hvdroxyirnino)methyllbenzyl}carbamateStep 1: tert-butyl 4-cyanobenzylcarbamate To a solution of 4-cyanobenzylamine hydrochloride (1.05 g; 6.25 mmol) in water (10 mL) was added sodium hydroxide (0.75 g; 18.75 mmol) and di-tert-butyldicarbonate (1 .49 g; 6.87 <n="114"/>mmol) and the mixture was stirred for 16 hours. The solid was collected by filtration and dried in a vacuum oven at 40°C for 48 hours. The title compound was isolated as a white solid (1 .35 g; 80percent). 1H NMR: (CDCI3, 400MHz) δ 7.62 (2H, d, J = 8.1 Hz), 7.39 (2H, d, J = 8.0 Hz), 4.97 (1 H, s), 4.37 (2H, d, J = 6.2 Hz), 1.46 (9H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: With sodium hydroxide In water at 25 - 28℃; Stage #2: at 25 - 30℃; |
4-Cyanobenzylamine hydrochloride salt (CBA HCl) (200 g, 1.19 mol) was dissolved in 1.25 L of distilled deionised water (6.25 volumes) in a 5 L reactor with a mantle temperature of 25 0C. At 25 0C, the solution was clear within 15 minutes. To the clear solution was added a solution of 52 g (1.1 eq.) of NaOH in 400 mL of water. The solution was added at a rate of 10-15 mL/min. A small temperature increase (~3 °C) was noted. A large amount of precipitate (the free amine) appeared during the addition. After the addition, the pH of the mixture was >12.A solution of BoC2O (285 g, 1.30 mol, 1.1 eq.) in MeOH (200 mL) was added drop- wise to the white suspension at an average rate of ~10 mL/min. Carbon dioxide evolution and a small temperature increase (5 °C over 30 min) was noted during the addition. As the addition continued, the consistency of the slurry/suspension changed as the insoluble amine was converted to the insoluble Boc-protected amine. EPO <DP n="17"/>The reaction was followed by taking samples of the supernatant in the reactor and comparing the peak area of the starting material with a calibration curve of the starting material (HPLC column: Symmetry Shield RP8, 3.5 μm, 50 mm; 205 and 230 nm - see Example 3 for more details). A 98percent conversion was obtained 6 hours after the addition of Boc2O was complete. The reaction was left overnight to obtain a 99percent conversion. The slurry was filtered and the solid washed with 2 x 500 mL water. The material was dried under vacuum at 40 °C to give Boc-CBA (265g, 97percent yield, 98.7percent purity (HPLC by analogy to Example 3, no Boc2O detected) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium hydroxide In tetrahydrofuran; methanol; water | B) Preparation of N-Boc-p-(aminomethyl)benzonitrile. To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid. |
94% | With sodium hydroxide In tetrahydrofuran; methanol; water | B) Preparation of N-Boc-p-(aminomethyl)benzonitrile To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid. |
94% | With sodium hydroxide In tetrahydrofuran; methanol; water | B) Preparation of N-Boc-p-(aminomethyl)benzonitrile To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid. |
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