Putrescine → Benzyl N-(4-aminobutyl)carbamate

Participants

Reaction Steps

To a solution of 147 g of 1,4-diaminobutane in 490 ml of methylene chloride, a solution of 41 ml of benzyl chloroformate in 84 ml of methylene chloride was added dropwise at 0° over a period of 1 hour. The mixture was stirred at 0° for 1 hour, then washed twice with water and extracted four times with 150 ml of 4N hydrochloric acid. The acidic extracts were washed with methylene chloride, basified with 450 ml of 22% of sodium hydroxide and extracted four times with methylene chloride. The organic extracts were dried over magnesium sulfate and evaporated to give 4-benzyloxycarbonylamino-1-butylamine, having NMR peaks at δ=7.3, 5.05 and 2.6 ppm.

Provenance & Evidence