Reaction #452480

Reaction equation

1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine

2-chloroquinoline

→

product

Yield 12.4%

1-(2-(2-Quinolinylamino)ethyl)-4-(2-methoxyphenyl)piperazine

Yield 12.4%

Solvents

hydrochloric acid

Conditions

Workup

1. 1
   Washwashed with dichloromethane (3×100 ml)
2. 2
   Extractionextracted into dichloromethane (3×100 ml)
3. 3
   Dryingdried (MgSO4)
4. 4
   Otherthen evaporated in vacuo
5. 5
   Otherto give a brown oil
6. 6
   OtherThe oil was purified by chromatography [alumina; ethyl acetate-toluene (1:4)]

Procedure

1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine (9.4 g, 40 mmol) and 2-chloroquinoline (6.5 g, 40 mmol) were heated at 160° C. for 3 h, then at 120° C. for 18 h in a sealed vessel. The resultant brown tar was taken up into dilute hydrochloric acid (300 ml), washed with dichloromethane (3×100 ml) basified with sodium hydroxide, extracted into dichloromethane (3×100 ml), dried (MgSO4) then evaporated in vacuo to give a brown oil. The oil was purified by chromatography [alumina; ethyl acetate-toluene (1:4)] to give the product (1.8 g) as a clear oil.

Source