HCID 56615476, compound → HCID 15610185, compound

Participants

Reaction Steps

942 g (3.79 moles) of 3,12-dipropyl-1,2-diaza-1,5,9-cyclododecatriene (diastereoisomer mixture) are dissolved in a stirred autoclave in 3800 ml of tert-butanol. After addition of 90 g of a rhodium/alumina catalyst (5% by weight), hydrogen is introduced up to a pressure of 130-150 bar and hydrogenation is effected at 150°-180° C. until the uptake of hydrogen is complete. After cooling, excess hydrogen is blown off, the suspension is sucked from the autoclave and the catalyst is collected by suction over a small amount of hyflo (filter aid). The filtrate is concentrated by rotary evaporation and the product is purified by distillation, yielding as main fraction 462 g (48% of theory) of 4,13-diaminohexadecane as a colourless oil [b.p. 132°-135° C./0.01 torr; nD20. 1.4590; IR spectrum (liquid) includes bands at 3278 and 1613 cm-1 ].

Provenance & Evidence