In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H11NO2
To a solution of the benzyl amine (179 mg, 1.08 mmol) and DIPEA (0.45 ml, 2.6 mmol) in CH2Cl2 (5 ml) was carefully added triphosgene (150 mg, 0.51 mmol) and the resulting solution was stirred at room temperature for 20 minutes (Majer, P.; Randad, R.S. J Org. Chem., 1994, 59, 1937-1938). A solution of 4-[(thiophen-3-ylmethyl)-amino]-piperidine- 1-carboxylic acid tert-huty ester (455 mg, 1.53 mmol) in CH2Cl2 (2 ml) was then added and the reaction was stirred at room temperature for an additional 18 hours. The mixture was diluted with saturated aqueous NaHCO3 (25 ml) and was extracted with CH2Cl2 (20 ml X 3). The combined organic solution was washed with brine (50 ml), was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/Et2O, 9:1, increased to 3:1) gave the urea as a light yellow foam (236 mg, 45%). 1H NMR (CDCl3) delta 1.43 (s, 9H), 1.44-1.58 (m, 2H), 1.69-1.79 (m, 2H), 2.71-2.85 (m, 2H), 3.89 (s, 3H), 4.09-4.24 (m, 2H), 4.33 (s, 2H), 4.39 (d, 2H, J= 5.8 Hz), 4.54 (tt, IH, J= 12.0, 3.7 Hz), 4.80 (t, IH, J= 5.7 Hz), 6.95 (d, IH, J= 4.8 Hz), 7.07 (d, IH, J- 1.5 Hz), 7.13 (d, 2H, J= 8.5 Hz), 7.34 (dd, IH, J= 5.0, 2.9 Hz), 7.91 (d, 2H, J- 8.5 Hz).
The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
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