Methylamine → HCID 67813946, compound

Participants

Reaction Steps

687 mg (1.99 mmol) of 2-{[(4-fluorophenyl)sulphanyl]methylene}-5-hydroxy-N-(4-methylphenyl)-pentanamide (prepared by the method described in WO 2010/070910) are dissolved in 25 ml of dichloromethane, and 828 mg (3.98 mmol) of phosphorus pentachloride are added. After 12 h of stirring at room temperature, all volatile components are removed under reduced pressure and the residue is suspended in 9 ml of triethylamine. 36.4 mg (0.297 mmol) of DMAP and 4.97 ml of 2M methanamine in THF are added to the reaction mixture. The mixture is stirred in a CEM microwave at 80° C. for 60 min (divided into three microwave vessels). The reaction mixture is diluted with water and extracted with ethyl acetate, and the organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 7.6 mg of N-(3-{[(4-fluorophenyl)sulphanyl]methylene}-1-methylpiperidin-2-ylidene)-4-methylaniline.

Provenance & Evidence