N-methyl compounds
N-methyl compounds are important building blocks in Medicinal Chemistry.
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Synthesis of N-methyl compounds
1.
2-bromoaniline (5g, 29.1 mmol, 2 eq) was dissolved in THF (30 mL). A solution of n-BuLi (1.6 M in hexane, 9.1 mL, 14.55 mmol, 1.0 eq) was added slowly at �0 °C and the resulting red mixture was stirred for 15 min at the same temperature. After cooling to �0 °C, iodomethane (0.91 mL, 14.6 mmol, 1.0 eq) was added slowly and the mixture was allowed to warm to rt and stirred for additional 14 h at rt. The mixture was quenched by adding H2O (20 ml) and the organic phase was separated. The aqueous phase was extracted with EtOAc (3 x 30 mL) and the combined organic phases were washed with sat. NaHCO3-solution dried over MgSO4 and the solvents were evaporated under reduced pressure. After purification by flash chromatography (silica, pentane/EtOAc = 50:1) the pure product was obtained as a yellow liquid (2.41 g, 13.0 mmol, 89%).
2.
A mixture of bromobenzene (10 mmol, 1.570 g), 30 % aqueous methylamine solution (5.4 mL, 50mmol), copper catalyst, and a stirring bar was sealed in a 30 mL screwed tube and stirred electromagnetically in an oil bath and heated to 80â€?00 °C. As the reaction proceeded, most of the copper powder was dissolved gradually. After the reaction completed or underwent to the time stated in Table 1, the reaction mixture was cooled to room temperature and ethyl acetate (20 mL) was added to extract the aryl amine. The organic layer was separated and the aqueous layer was extracted by ethyl acetate (3×10 mL). The combined extracts was dried by anhydrous sodium sulfate and the solvent was removed under reduced pressure to give the crude product that was purified by silica gel column chromatography (eluent: petroleum ether /ethyl acetate) to give the pure product.
3.
To a solution of methanol (50 mL) and 2-bromobenzaldehyde (4.02 g, 22 mmol) was added a 40% aqueous solution of methylamine (2.44 mL, 28 mmol). After stirring at room temperature for 15 min, the solution was cooled to 0 oC prior to adding sodium borohydride (0.41 g, 11 mmol) portion wise. The resulting solution was stirred at room temperature for 1 h. After addition of water (50 mL), methanol was evaporated under vacuum and the resulting aqueous phase extracted with CH2Cl2 (3X50 mL). The combined organic layers are dried (MgSO4) and evaporated affording (2-Bromo-benzyl)-methyl-amine as a colorless oil (3.81 g, 89%).
4.
The p-aminophenol (1 g) is dissolved in a mixture consisting of dimethyl carbonate (hereafter referenced as DMC) (10 ml) and DME (35 ml). The NaY-faujasite (1 g) is added to the resulting mixture and heating to 90.deg.C is performed. The reaction, which is monitored by gas chromatography optionally associated with mass spectrometry, is completed after 7 hours, providing a practically quantitative conversion. At this point the solid catalyst is eliminated by filtration and the monomethylated product can thus be recovered. Instrumental analysis performed after solvent evaporation yielded a selectivity value of 99 percent for the N-monomethylated product and a total yield of 91 percent.
The application of N-methyl compounds.
N-methyl compounds often appear in Brand Name Drugs, such as:
Cymbalta Strattera Fluoxetine Sertraline
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