Reaction #452482

Reaction equation

homopiperazine

2-chloromethyl-quinoline hydrochloride

triethyl-amine

→

title compound

Yield 39.3%

1-(2-quinolylmethyl)homopiperazine

Yield 39.3%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONWater was added to the residue
3. 3
   WashAfter the resulting mixture was washed three times with ethyl ether, sodium chloride
4. 4
   workup.ADDITIONwas added to the water layer
5. 5
   Extractionfollowed by extraction four times with chloroform-methanol (2:1)
6. 6
   WashThe extract was washed with an aqueous solution of sodium chloride
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedure

After a mixture consisting of 2-chloromethyl-quinoline hydrochloride (63.16 g, 295 mmol), triethyl-amine (29.85 g, 295 mmol), homopiperazine (50.08 g, 591 mmol) and ethanol (600 ml) was stirred at room temperature for 2 days, the solvent was distilled off under reduced pressure. Water was added to the residue. After the resulting mixture was washed three times with ethyl ether, sodium chloride was added to the water layer, followed by extraction four times with chloroform-methanol (2:1). The extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby 28.00 g of the title compound were obtained as a yellow oil (yield: 39.3%).

Source