Ethyl chloroformate → N-methyl-N-[2-(2,6-dichloro-phenyl)-ethyl]-amine

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Reaction Steps

2-(2,6-Dichlorophenyl)ethylamine (1 ml, 0.00663 mol) and TEA (1.4 ml, 1.5 eq) were dissolved in THF (20 ml) and cooled in an ice-water bath. Ethyl chloroformate (0.95 ml, 1.5 eq) was added slowly and the mixture stirred at rt for 2 h. NH4Cl (sat) was added and the mixture extracted with EtOAc, the combined extracts were washed with NH4Cl (sat), and dried (MgSO4). The organic solvent was removed and the residue dissolved in Et2O (5 ml). This solution was slowly added to a slurry of LiAlH4 (530 mg, 2 eq) in Et2O (15 ml) at −78° C. The mixture was allowed to slowly warm to rt and stirred overnight. The mixture was cooled in an ice-water bath and water (0.53 ml), 15% NaOH (0.53 ml), and water (1.5 ml) added sequentially. The mixture was stirred vigorously for 30 min and the resulting slurry filtered. The filtrate was concentrated under reduced pressure to give 1.2 g of [2-(2,6-dichlorophenyl)ethyl]methylamine.

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