Potassium Carbonate → HCID 14720349, compound

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Reaction Steps

A 2.5 g. portion of 3-(4-chloro-2-methoxyphenylaminomethyl)pyridine was dissolved in 20 ml. of dichloromethane, and to it were added 2.1 g. of potassium carbonate and 1.2 ml. of methanesulfonyl chloride. The mixture was stirred with gentle heating for 2 days, and was then extracted with aqueous sodium bicarbonate. The organic phase was dried and evaporated under vacuum, and the residue was redissolved in dichloromethane and 2.6 g. of methanesulfonic anhydride was added. The mixture was stirred at ambient temperature for several days, and another 2.6 g. of the anhydride was added, together with 2.5 g. of additional starting amine. The mixture was stirred at ambient temperature for several days more, and was then diluted with 20 ml. of aqueous sodium bicarbonate and 15 ml. of dichloromethane, and the organic phase was dried over magnesium sulfate and evaporated to an oil. The oil was taken up in chloroform and chromatographed over silica gel, eluting with chloroform, to obtain 1.17 g. of the desired compound, m.p. 121°-123°.

Provenance & Evidence