Hydrochloric Acid → tert-Butyldiisobutylamine

Isobutyryl chloride (10.90 g, 0.1 mol) was added to a solution of tert-butylisobutylamine (25.85 g, 0.2 mol) in tetrahydrofuran (150 ml) at room temperature and stirred for 1 h. Solids were filtered off and washed with tetrahydrofuran ( 2×25 ml). N, N-tert-butylisobutyl-2-methylpropionamide was isolated by distillation to yield 18.50 g, (90%), bp 59-60° C./1.3 mm Hg. A 1 M borane-tetrahydrofuran solution (100 ml, 0,10 mol) was added dropwise to a solution of the amide (17.95 g, 90 mmol) in tetrahydrofuran (50 ml) at room temperature and the mixture refluxed for 1 h. Water (5 ml) was added after cooling, followed by a slow addition of 6 M hydrochloric acid (60 ml). Tetrahydrofuran was distilled off and solid sodium hydroxide (20.00 g, 0.5 mol) was added. The organic layer was separated and the aqueous solution was extracted with n-pentane (50 ml). The organic solutions were combined, dried over anhydrous magnesium sulfate, and the product was isolated by distillation to yield 14.24 g, (85%), bp 34-35° C./1.5 mm Hg; 1H NMR (CDCl3) δ0.84 (d, J=6.6 Hz, 12H, CH3), 1.01 (s, 9H, CH3), 1.58 (nonet, J=6.6 Hz, 2H, CH), 2.14 (d, J=6.6 Hz, 4H, CH2),

1. customto yield 18.50 g, (90%), bp 59-60° C./1.3 mm Hg
2. temperaturethe mixture refluxed for 1 h
3. temperatureafter cooling
4. distillationTetrahydrofuran was distilled off
5. customThe organic layer was separated
6. extractionthe aqueous solution was extracted with n-pentane (50 ml)
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe product was isolated by distillation
9. customto yield 14.24 g, (85%), bp 34-35° C./1.5 mm Hg

ORD record

ord-df2db2bdaeb14fbc950539650db00fff

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248885B1