Adding a certain compound to certain chemical reactions, such as: 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6851-80-5, Application In Synthesis of 1-(2-Methoxyphenyl)-N-methylmethanamine
General procedure FStep 1 / synthesis of substituted N-benzyl-4-chloro-N-methylbutanamide : Triethylamine (1 eq) and 4-chlorobutyryl chloride (1 eq) were added to a solution of the substituted N-methylbenzylamine (1 eq) in dichloromethane (1.3 ml_/ mmol). The mixture was stirred 3 hours at room temperature then water was added. The resulting mixture was extracted 3 times with dichloromethane, the combined organic layers were dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the substituted N-benzyl-4-chloro-N-methylbutanamide. Step 2 / alkylation of thiols with substituted N-benzyl-4-chloro-N-methylbutanamide: Anhydrous potassium carbonate (1.5eq) and substituted N-benzyl-4-chloro-N- methylbutanamide (1 eq) were added to a solution of the thiol derivative (1 eq) in acetonitrile (6 mL / mmol). The mixture was refluxed overnight then water and ethyl acetate was added after cooling. The mixture was extracted 3 times with ethyl acetate, the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the thio-ether.The following compounds were prepared according general procedure F :Example 138 : 4-[(3,4-Difluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamidePrepared from commercial 3,4-difluorothiophenol and commercial 2-methoxy-N- methylbenzylamine in 27% yield.NMR-1H (CDCI3) : delta (ppm) 7.32-6.85 (m, 7H) ; 4.55 (d, 2H) ; 3.84-3.82 (m, 3H) ; 3.03-2.92(m, 5H) ; 2.50 (t, 2H) ; 2.04-1 .94 (m, 2H) MS (ESI+) : m/z = 366 [M+H]+
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Reference:
Patent; CELLVIR; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S); BENAROUS, Richard; BARBEY-TREVE, Sabine; PARIS, Jean-Marc; BERRUT, Sebastien; BERLIOZ-TORRENT, Clarisse; EMILIANI, Stephane; WO2010/66847; (2010); A1;,
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