N',N'-dimethyl-N-phenylethane-1,2-diamine

Conditions: temp:100.01; pressure:0.00; stir:

Procedure: In a 50 mL round-bottomed flask (t=g) was unsym-Dimethylethylenediamine (1.080 mL, 9.80 mmol), Iodobenzene (0.549 mL, 4.90 mmol), and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.449 g, 0.49 mmol)Cesium carbonate (2.396 g, 7.35 mmol) andCesium carbonate (2.396 g, 7.35 mmol) were added. in DMF (10 mL) ([VOLUME]) to give a brown suspension. Reaction stirred over night at 100°C. no reaction.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 24.6 grams (0.15 mole) of N,N-dimethyl-N'-phenyl-ethylenediamine and 18.2 grams (0.18 mole) of triethylamine in 500 milliliters of tetrahydrofuran (THF) is cooled to 0° C. and 39.8 grams (0.18 mole) of 5-methyl-3-phenyl-4-isoxazole carbonyl chloride in 100 milliliters of tetrahydrofuran is added dropwise. After the addition is complete, the mixture is warmed to room temperature and stirred for 4 hours. The resulting suspension is filtered and the THF removed in vacuo. The residue is dissolved in methylene chloride and washed with 2N sodium hydroxide and water and then dried over magnesium sulfate. The mixture is filtered and the solvent removed by evaporation. The residue is then treated with hexane to yield crystals of N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide; M.P. 88°-89° C. After the addition the mixture is warmed to room temperature The resulting suspension is filtered the THF removed in vacuo The residue is dissolved in methylene chloride washed with 2N sodium hydroxide and water dried over magnesium sulfate The mixture is filtered the solvent removed by evaporation The residue is then treated with hexane

Conditions: temp:100.01; pressure:0.00; stir: