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

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).

1. temperaturewas refluxed
2. extractionthe mixture was extracted with n-pentane (2×50 ml)
3. customThree layers were formed
4. customAdiponitrile (the middle layer) was recovered
5. dry with materialThe pentane solution was dried over anhydrous magnesium sulfate
6. customthe product was isolated by distillation
7. customto yield 9.5 g, (74%), bp 45-47° C./40 mm Hg

ORD-Eintrag

ord-2e6182b2560f49de91847f7ddb264d2c

Quelldatensatz

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06248885B1