Dimethylamine → N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

Participants

Reaction Steps

A solution of 1 equivalent of N-[2-[4-(4-carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide (see Example 31) in tetrahydrofuran is treated with 10 eq. of thionyl chloride and stirred at room temperature for 16 hours. The mixture is then concentrate in vacuo, dissolved in dichloromethane and added to a 0° C. solution of 1 eq. of dimethylamine in dichloromethane. The mixture is stirred at 0° C. for 2 hours. and 10% aqueous sodium bisulfate is added. The organic layer is separated and the aqueous layer is extracted two times with dichloromethane. The combined organic extracts are dried over NaSO4, filtered and concentrate in vacuo to provide the crude material. Chromatography of the crude material affords the title compound.

Provenance & Evidence