Reaction #3940

Reaction equation

1-bromo-3-chloropropane

1-(4-chlorobenzyl)homopiperazine

potassium hydroxide

→

1-(4-chlorobenzyl)-4-(3-chloropropyl)homopiperazine

Yield 42.0%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Otheran additional 30 minutes
2. 2
   Otherat room temperature
3. 3
   Extractionthe product was extracted with ether
4. 4
   Dryingthe extract was dried (magnesium sulfate)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherFinal purification
7. 7
   Otherthe solvent was removed in vacuo

Procedure

15.7 g of 1-bromo-3-chloropropane were added to a cooled solution of 15.0 g of 1-(4-chlorobenzyl)homopiperazine and 12.0 g of potassium hydroxide in 50 ml of dimethyl sulfoxide. The mixture was stirred at 5°-10° C. for one hour, and then an additional 30 minutes at room temperature. After the addition of ice water, the product was extracted with ether, and the extract was dried (magnesium sulfate) and concentrated in vacuo. Final purification was effected on a silica gel column (methylene chloride:methanol, 9:1), and the solvent was removed in vacuo to give 8.4 g (42% of theory) of 1-(4-chlorobenzyl)-4-(3-chloropropyl)homopiperazine as an oil.

Source