Allylamine → 8-Azabicyclo[4.3.0]non-2-ene

HRID 1489526Notes

Reaction equation

HRID 1489526 reaction equation
[NH2:1][CH2:2][CH:3]=[CH2:4].Br[CH2:6]/[CH:7]=[CH:8]/[CH:9]=[CH2:10]>>[CH:9]12[CH2:10][NH:1][CH2:2][CH:3]1[CH2:4][CH2:6][CH:7]=[CH:8]2

Participants

3

Procedure

Initially introduce 228 g (4.0 mol) of 1-amino-2-propene. Add 58.8 g (0.4 mol) of (E)-1-bromo-2,4-pentadiene (title compound from Example A.1.) dropwise with stirring. Keep the internal temperature in the range from 20°-30° C. by cooling. Stir at room temperature for 5 h. Concentrate the mixture at 150 mbar. Add 20 g (0.5 mol) of sodium hydroxide dissolved in 200 ml of water, extract twice with 100 ml of methylene chloride each time, dry with sodium sulphate, add 0.1 g of 4-hydroxyanisole, concentrate and distil at 40 mbar. For stabilization, 10-20 ppm of 4-hydroxyanisole are added to the distillate.

Sources & evidence

ORD record
ord-cd3a412e553c4632afce35f7c049ddc3
Source dataset
uspto-grants-1997_10
Patent number
US05679675

Reaction notes

Loading…