benzyl N-[[4-(aminomethyl)phenyl]methyl]carbamate

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

Procedure: A solution of 1,4-bis(aminomethyl)benzene (10.0 g, 74 mmol) and triethylamine (9.8 ml, 74 mmol) in dichloromethane (480 ml) was cooled to 0° C. and treated with a solution of benzylchloroformate (10.5 ml, 74 mmol) in dichloromethane (250 ml). The resulting mixture was allowed to warm gradually to room temperature of a period of 16 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (450 ml) and 1M aqueous sodium hydroxide (300 ml). The resulting biphasic mixture was filtered and the organic phase separated, dried (magnesium sulfate) and reduced in vacuo to give a waxy solid. Trituration with hot ethyl acetate followed by concentration of the liquors gave the title compound as a waxy solid (7.4 g). The solvent was removed in vacuo the residue partitioned between ethyl acetate (450 ml) and 1M aqueous sodium hydroxide (300 ml) The resulting biphasic mixture was filtered the organic phase separated dried (magnesium sulfate) to give a waxy solid

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

Procedure: A solution of benzylchloroformate (10.48 ml, 74 mmol) in dichloromethane (250 ml) was added to an ice-cooled solution of 4-aminomethyl benzylamine (10 g, 74 mmol) and triethylamine (9.77 ml, 74 mmol), in dichloromethane (480 ml) over 90 minutes. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (450 ml) and 1M sodium hydroxide solution (300 ml). The resulting mixture was filtered, the layers separated and the organic phase dried over magnesium sulphate and evaporated under reduced pressure. The residue was dissolved in hot ethyl acetate, the solution cooled in an ice-bath, the resulting solid filtered off, and the filtrate evaporated under reduced pressure to afford the title compound as a white solid, 7.44 g. The mixture was concentrated under reduced pressure the residue partitioned between ethyl acetate (450 ml) and 1M sodium hydroxide solution (300 ml) The resulting mixture was filtered the layers separated the organic phase dried over magnesium sulphate evaporated under reduced pressure The residue was dissolved in hot ethyl acetate the solution cooled in an ice-bath the resulting solid filtered off the filtrate evaporated under reduced pressure