BUTYL-l,3-DIAMINOPROPANE

Submitted by R. O. Hutchins and B. E. Maryanoff Checked by Abraham Pinter and Ronald Breslow 

tert-Butylmalononitrile. In a dry 2-1. three-necked flask equipped with a thermometer, mechanical stirrer, and a Claisen adapter fitted with a dropping funnel and condenser protected with a drying tube is placed 200 ml. of nitromethane (Note 1). The flask is cooled to 0° in an ice-salt bath (Note 2), and anhydrous powdered aluminum chloride (90.0 g., 0.68 mole) is added with slow stirring through a powder funnel that temporarily replaces the thermometer. The temperature may rise to ca. 50° but quickly drops to 0°. Malononitrile (45.0 g., 0.68 mole) (Note 3) in 50 ml. of nitromethane is added through the dropping funnel at a rate such that the temperature is kept below 10° (approximately one hour), followed by slow dropwise addition of tert-butyl chloride (Note 4) (150 g., 1.62 moles) in 50 ml. of nitromethane at a rate such that the temperature is maintained 

2-tert-Butyl-1,3-diaminopropane. A dry 500-ml. threenecked flask fitted with a magnetic stirrer, nitrogen inlet, dropping funnel, and condenser attached to an acetone gas trap (Note 6) is flushed with dry nitrogen for 30 minutes and charged with purified ferf-butylmalononitrile (30.5 g., 0.25 mole), sodium borohydride (17.5 g., 98% assay, 0.453 mole), and 150 

Kisher Scientific Company certified reagent grade was used without further purification from a freshly opened bottle. 

Malononitrile was obtained from Eastman Organic Chemicals and distilled prior to use, b.p. 80-82° (3 mm.). 

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