(3-chloro-2-methylphenyl)methanamine

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.15 g of N-(3-chloro-2-methylbenzyl)phthalimide was dissolved in 20 mL of methanol, and 5 mL of hydrazine monohydrate was added thereto at room temperature. Thereafter, it was warmed to 80° C., followed by continuously reacting overnight. After completion of the reaction, the reaction liquid was left to be cooled, and water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 628 mg (yield 100%) of a title compound as a colorless clear oily substance. at room temperature After completion of the reaction the reaction liquid was left to be cooled followed by extraction with chloroform The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: To 1,3-dimethyl-2-oxo-4-imidazolidinecarboxylic acid (6.000 ml, 0.600 mmol) (0.1M solution in dichloromethane) was added the N-ethylmorpholine (0.380 ml, 3.00 mmol), 1-hydroxybenzotriazole hydrate (110 mg, 0.720 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg, 0.720 mmol), and the reaction stirred at RT under argon for 10 minutes. [(3-Chloro-2-methylphenyl)methyl]amine (103 mg, 0.660 mmol) was then added and the reaction left to stir at RT under argon overnight. The reaction mixture was diluted with dichloromethane (15 ml) and then the solution was washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), 3N citric acid solution (20 ml), brine (20 ml) and then dried over magnesium sulphate. The solvent was evaporated in vacuo. The residue was purified by mass-directed automated HPLC. Fractions containing product were combined and solvent evaporated in vacuo, co-evaporated with diethyl ether to give the N-[(3-chloro-2-methylphenyl)methyl]-1,3-dimethyl-2-oxo-4-imidazolidinecarboxamide as a white solid (50 mg, 26.8% yield). LC/MS [M+H]+=296, retention time=1.96 minutes the reaction left to stir at RT under argon overnight the solution was washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), 3N citric acid solution (20 ml), brine (20 ml) dried over magnesium sulphate The solvent was evaporated in vacuo The residue was purified Fractions containing product solvent evaporated in vacuo, co-evaporated with diethyl ether

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