2-Chlorobenzyl chloride → HCID 57682471, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml three-necked flask, 5 g (0.04 mol) of 1,5-diazabicyclo[4.3.0]non-5-ene are dissolved in 100 ml of tetrahydrofuran, and at room temperature 6.48 g (0.04 mol) of 2-chlorobenzyl chloride are slowly added with stirring. A colourless suspension is formed which is stirred overnight. The suspension is then filtered, the salt isolated by filtration is washed, and the washed salt is suspended in 100 ml of tetrahydrofuran. Added to this suspension in portions is 0.76 g (0.02 mol) of lithium aluminium hydride. After the end of the addition, the reaction mixture is stirred at room temperature overnight. It is then cooled to 0° C. and, dropwise, 0.8 g of water, then 0.8 g of 10% strength sodium hydroxide solution and a further 2.4 g of water are added. The resulting suspension is stirred at room temperature for 30 minutes and then filtered. The filter cake is washed with tetrahydrofuran and the combined organic phases are dried and concentrated on a rotary evaporator. This gives 7.15 g of 5-(2-chlorobenzyl)-1,5-diazabicyclo[4.3.0]nonane as a colourless oil.

Provenance & Evidence