Allylamine → 8-Azabicyclo[4.3.0]non-2-ene
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]2Participants
3
Procedure
Introduce 228 g (4.0 mol) of 1-amino-2-propene. Add dropwise with stirring 58.8 g (0.4 mol) of (E)-1-bromo-2,4-pentadiene (title compound of Example A.1.). Keep the internal temperature in a range of 20°-30° C. by means of cooling. Stir for 5 h at room temperature. Concentrate batch at 150 mbar. Add 20 g (0.5 mol) of sodium hydroxide, dissolved in 200 ml of water, extract the mixture twice using in each case 100 ml of methylene chloride, dry using sodium sulphate, add 0.1 g of 4-hydroxyanisole, concentrate and distil at 40 mbar. 10-20 ppm of 4-hydroxyanisole are added to stabilize the distillate.
Workup
- additionAdd dropwise
Sources & evidence
- ORD record
- ord-09d8670013a6436586a9a5449f31f6c4
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05854241
Reaction notes
Loading…