Glycerol → tert-Butylisobutyl-n-propylamine

HRID 1067905

Reaktionsgleichung

Reaktionsgleichung von HRID 1067905
[C:1]([NH:5][CH2:6][CH:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].I[CH2:11][CH2:12][CH3:13].OCC(CO)O.[OH-].[K+]>>[C:1]([N:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 753GlycerolHCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 527145N-tert-butyl-2-methylpropan-1-amine

Produkt 1

HCID 21195175tert-Butylisobutyl-n-propylamine

Versuchsvorschrift

A mixture of tert-butylisobutylamine (19.39 g, 0.15 mol), 1-iodopropane (20.40 g, 0.12 mol) and glycerol (5.53 g, 60 mmol) was refluxed for 40 h. Aqueous 8 M potassium hydroxide (30 ml, 0.24 mol) was added, the organic layer was separated and the aqueous layer 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 12.52 g, (61%), bp 72-73° C./18 mm Hg; 1H NMR (CDCl3) δ0.80 (t, J=6.2 Hz, 3H, CH3), 0.84 (d, J=6.6 Hz, 6H, CH3), 1.01 (s, 9H, CH3), 1.40 (sextet, J=6.2 Hz, 2H, CH2), 159 (nonet, J=6.6 Hz, 1H, CH), 2.16 (d, J=6.6 Hz, 2H, CH2), 2.34 (m, 2H, CH2).

Aufarbeitung

  1. temperaturewas refluxed for 40 h
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with n-pentane (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe product was isolated by distillation
  6. customto yield 12.52 g, (61%), bp 72-73° C./18 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-6a56ebd3eca14a26aa771b6ccc426d0c
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248885B1

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