Reaction #2303

Reaction equation

4-(piperazin-1-yl)anisole

4-chloropyridine hydrochloride

ammonia

→

4-[4-(4-pyridyl)-piperazin-1-yl]anisole

Yield 31.0%

Solvents

water

Conditions

Workup

1. 1
   Temperatureheated at 160°-170° C. (bath temperature) for 7 minutes
2. 2
   OtherThe solid obtained
3. 3
   Temperatureon cooling
4. 4
   ExtractionThe solid precipitate was extracted into ethyl acetate
5. 5
   Extractionthe organic extract
6. 6
   Washwashed with water
7. 7
   Filtrationfiltered through phase
8. 8
   Otherseparating paper (Whatman 1PS)
9. 9
   Otherevaporated
10. 10
    OtherThe residue was recrystallised from ethanol

Procedure

4-(piperazin-1-yl)anisole (4.24 g) and 4-chloropyridine hydrochloride (3.35 g) were intimately mixed and heated at 160°-170° C. (bath temperature) for 7 minutes. The solid obtained on cooling was dissolved in water (75 ml) and the solution basified with aqueous ammonia. The solid precipitate was extracted into ethyl acetate and the organic extract washed with water, filtered through phase separating paper (Whatman 1PS) and evaporated. The residue was recrystallised from ethanol to give 4-[4-(4-pyridyl)-piperazin-1-yl]anisole (1.84 g) as a solid: m.p. 165°-167° C.; NMR (CDCl3) δ8.3(2H,d); 6.86(4H,m); 6.71(2H,d); 3.78(3H,s); 3.46(4H,m); 3.2(4H,m).

Source