Tert-Butylamine → N-tert-butyl-2-methylpropan-1-amine

Participants

Reaction Steps

A mixture of tert-butylamine (10.97 g, 0.15 mol), isobutyl bromide (13.70 g, 0.1 mol), adiponitrile (10.81 g, 0.1 mol) and tetrabutylammonium iodide (1.85 g, 5 mmol) was refluxed with stirring for 12 hours. Aqueous 5 M potassium hydroxide (30 ml, 0.15 mmol) was added and the mixture was extracted with n-pentane (2×50 ml). Three layers were formed. Adiponitrile (the middle layer) was recovered. The pentane solution was dried over anhydrous magnesium sulfate and the product was isolated by distillation to yield 9.5 g, (74%), bp 45-47° C./40 mm Hg; 1H NMR (CDCl3) δ0.91 (d, J=6.5 Hz, 6H, CH3), 1.08 (s, 9H, CH3), 1.64 (sep, J=6.5 Hz, 1H, CH), 2.34 (d, J=6.5 Hz, 2H, CH2).

Provenance & Evidence