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1-Propylbutyl isocyanate: This intermediate was prepared from commercially available 4-aminoheptane by the procedure of V. S. Goldesmidt and M. Wick, Liebigs Ann. Chem., 575, 217 (1952). (b) 1-Ethyl-1-(2-propenyl)-3-butenyl isocyanate: A solution of propionitrile (14.5 g, 264 mmol) in dry Et2O (40 mL) was added dropwise to 1.0M allyl magnesium bromide/Et2O (880 mL). The reaction mixture was mechanically stirred at reflux for 2 h, after which time it was cooled to 0°. A saturated aqueous solution of NH4Cl (320 mL) was added cautiously to the cooled reaction mixture. The organic phase was separated, dried (MgSO4), cooled to 0° and then mixed at the same temperature with 1M HCl/Et2O (200 mL). The resulting solid was collected and dried under reduced pressure (ca 27 g). The latter material dissolved in CH2Cl2 (200 mL). The solution was washed with a 10% aqueous solution of Na2CO3 (2 X) and then brine, dried (MgSO4) and concentrated to dryness to afford a yellow oil. The oil was distilled (82°-85°/20 Torr) to give 1-ethyl-1-(2-propenyl)-3-butenylamine as a colorless liquid (11.6 g, 34%); 1H NMR(CDCl3) δ0.89 (t, J=7Hz, 3H), 1.39 (q, J=7 Hz, 2H), 2.11 (d, J=7 Hz, 2H), 5.06-5.14 (m, 4H), 5.80-5.89 (m, 2H).

1. temperatureat reflux for 2 h
2. temperatureafter which time it was cooled to 0°
3. customThe organic phase was separated
4. dry with materialdried (MgSO4)
5. temperaturecooled to 0°
6. additionmixed at the same temperature with 1M HCl/Et2O (200 mL)
7. customThe resulting solid was collected
8. customdried under reduced pressure (ca 27 g)
9. dissolutionThe latter material dissolved in CH2Cl2 (200 mL)
10. washThe solution was washed with a 10% aqueous solution of Na2CO3 (2 X)
11. dry with materialbrine, dried (MgSO4)
12. concentrationconcentrated to dryness
13. customto afford a yellow oil
14. distillationThe oil was distilled (82°-85°/20 Torr)