1-Bromo-3-chloropropane → 2,5-Diazabicyclo[2.2.1]heptane, 2-(3-chloropropyl)-5-phenyl-

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Reaction Steps

129 (1.0 g, 5.7 mmoles), 0.23 g (5.7 mmoles) of sodium amide and 20 mL of toluene are refluxed for 1 hour. After that, 0.93 g (5.7 mmoles) of 1-bromo-3-chloropropane in 10 mL of toluene are added dropwise over a period of 20 minutes and refluxed for 2 hours. After cooling, the reaction mixture is extracted with 2N HCl (2×50 mL) and the aqueous phase made alkaline with 30% sodium hydroxide and extracted with toluene (3×40 mL). Evaporation and bulb tube evaporation (boiling point at 0.05 mbar: 120°–130° C.) resulted in 0.97 g (70.4% of the theoretical yield) of 136 as a colorless oil.

Provenance & Evidence