Application of 38336-04-8, These common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Compound 12 was synthesized by the method described in Synth. Commun.,25, 907 (1995), and Compound 13 and Compound 2 were synthesized by the method described in J. Ned. Chem., 38, 1673 (1995). Succinic anhydride (150.1 mg, 1.5 mmol) was gradually added to a pyridine solution (2.0 ml) of each of Compounds 12, 13 and 2 (1.0 mmol) at room temperature, followed by stirring at 100C for 1.5 to 4 hours, respectively. The reaction solution was cooled to room temperature, and 2 mol/l hydrochloric acid was added thereto, followed by extraction with dichloromethane. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:3) to give each of Compounds 14 to 16, respectively (yield 92 to 100%). (Compound 14)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.51 (2H, t, J=7.0Hz), 2.69 (2H, t, J=7.0Hz), 3.49 (2H, t, J=5.0Hz), 3.59 (2H, t, J=5.0Hz), 4.54 (2H, s), 6.20 (1H, t, J=5.0Hz), 7.31-7.42 (5H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 175.8 (C), 172.5 (C), 137.4 (C), 128.1 (CHx2), 127.5 (CH×2), 127.5 (CH), 72.6 (CH2), 68.2 (CH2), 39.1 (CH2), 30.2 (CH2), 29.2 (CH2). (Compound 15)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.49 (2H, t, J=5.0Hz), 2.57 (2H, t, J=5.0Hz), 3.54 (2H, dd, J=7.2, 4.9Hz), 3.64 (2H, dd, J=7.2, 3.0Hz), 4.25-4.32 (1H, m), 4.50 (4H, s), 6.09 (1H, d, J=6.9Hz), 7.25-7.37 (10H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 175.8 (C), 171.6 (C), 137.7 (C×2), 128.3 (CHx4), 127.6 (CH×4), 127.6 (CH×2), 127.6 (C), 73.1 (CH2×2), 68.3 (CH2×2), 48.7 (CH), 30.6 (CH2), 29.6 (CH2). (Compound 16)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.06 (2H, t, J=5.0Hz), 2.44 (2H, t, J=5.0Hz), 3.50-3.82 (14H, m), 4.09-4.16 (1H, m), 4.50 (2H, s), 4.50 (2H, s), 6.82 (1H, d, J=6.5Hz), 7.25-7.36 (20H, m).13C-NMR (CDCl3, 300MHz) delta (ppm): 175.3 (C), 172.0 (C), 137.9 (C×2), 137.7 (C×2), 128.2 (CH×4), 128.2 (CH×4), 127.7 (CH×4), 127.6 (CH×4), 127.5 (CH×2), 127.4 (CH×2), 78.9 (CH×2), 73.4 (CH2×2), 73.2 (CH2×2), 70.5 (CH2×2), 69.9 (CH2×2), 68.4 (CH2×2), 49.6 (CH), 30.1 (CH2), 30.0 (CH2). NHS (126.6 mg, 1.1 mmol), EDC (412.7 mg, 2.0 mmol) and triethylamine (0.11 ml, 0.8 mmol) were added to a tetrahydrofuran solution (45 ml) of each of Compounds 14 to 16 (1.0 mmol) in this order at room temperature, followed by refluxing for 2 to 4 hours. Then, 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:10) to give Compounds 17 to 19, respectively (yield 53 to 90%). (Compound 17)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.61 (2H, t, J=7.0Hz), 2.87 (4H, s), 3.19 (2H, t, J=7.0Hz), 3.49 (2H, t, J=5.0Hz), 3.59 (2H, t, J=5.0Hz), 4.55 (2H, s), 6.13-6.25 (1H, m), 7.31-7.42 (5H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 170.1 (C×2), 169.1 (C), 168.2 (C), 137.8 (C), 128.5 (CH×2), 127.9 (CH××2), 127.9 (CH), 73.2 (CH2), 68.9 (CH2), 39.5 (CH2), 30.6 (CH2), 26.8 (CH2), 25.5 (CH2×2). (Compound 18)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.59 (2H, t, J=5.5Hz), 2.79 (4H, s), 2.98 (2H, t, J=5.5Hz), 3.54 (2H, dd, J=7.5, 5.0Hz), 3.64 (2H, dd, J=7.5, 3.0Hz), 4.27-4.34 (1H, m), 4.51 (4H, s), 5.95 (1H, d, J=6.8Hz), 7.25-7.39 (10H, m). 13C-NMR (CDCl3, 75MHz) delta (ppm): 169.3 (C), 168.7 (C×2), 167.9 (C), 137.9 (C×2), 128.2 (CH×4), 127.6 (CHx4), 127.5 (CH×2), 73.1 (CH2×2), 68.3 (CH2×2), 48.6 (CH), 30.7 (CH2), 26.7 (CH2), 25.5 (CH2×2). (Compound 19)1H-NMR (CDCl3, 400MHz) delta (ppm): 2.12 (2H, t, J=5.8Hz), 2.77-2.82 (6H, m), 3.51-3.82 (14H, m), 4.09-4.17 (1H, m), 4.50 (2H, s), 4.51 (2H, s), 6.68 (1H, d, J=7.0Hz), 7.27-7.35 (20H, m).13C-NMR (CDCl3, 75MHz) delta (ppm): 169.2 (C), 68.7 (C×2), 167.8 (C), 138.0 (C×2), 137.8 (C×2), 128.3 (CH×4), 128.2 (CH×4), 127.7 (CH×4), 127.6 (CH×4), 127.4 (CH×4), 79.0 (CH×2), 73.4 (CH2×2), 73.3 (CH2×2), 70.6 (CH2×2), 70.0 (CH2×2), 68.5 (CH2×2), 49.4 (CH), 29.8 (CH2), 26.5 (CH2), 25.0 (CH2×2). N-(8-aminooctyl)benzamide hydrochloride (compound Ra-H·HCl) was synthesized by the method described in Synthesis, 917 (1988). Compound Ra-H·HCl (284.8 mg, 1.0 mmol) and triethylamine (0.14 ml, 1.0 mmol) were added to a tetrahydrofuran solution (20 ml) of each of Compounds 17 to 19 and 6 (1.0 mmol) in this order at room temperature, followed by stirring at the same temperature for 3 to 6 hours. Then, 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate and then filtered. The solvent…
Statistics shows that 2-(Benzyloxy)-1-ethanamine is playing an increasingly important role. we look forward to future research findings about 38336-04-8.
Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; Tecno Network Shikoku Co.,Ltd.; EP1550651; (2005); A1;,
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