Reacción #2302

Ecuación de reacción

4-(4-(4-pyridyl)piperazin-1-yl)-phenol

sodium hydride

ethyl 4-bromobutyrate

→

title compound

Ethyl 4-[4-[4-(4-pyridyl)piperazin-1-yl]phenoxy]butyrate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hours
2. 2
   OtroSolvent was evaporated under reduced pressure
3. 3
   Otrothe residue was partitioned between ethyl acetate and water
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Filtraciónfiltered through phase
6. 6
   Otroseparating paper (Whatman 1PS)
7. 7
   Otroevaporated
8. 8
   OtroThe residue was purified by flash chromatography on silica
9. 9
   Lavadoeluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89)
10. 10
    Otrorecrystallised from ethyl acetate/hexane

Procedimiento

A stirred suspension of 4-(4-(4-pyridyl)piperazin-1-yl)-phenol (1.34 g) in dry DMF (20 ml) was treated with sodium hydride (60% dispersion in mineral oil, 0.21 g) and the mixture stirred for 1 hour. To the resulting solution was added ethyl 4-bromobutyrate and the mixture was stirred for 16 hours. Solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, filtered through phase separating paper (Whatman 1PS) and evaporated. The residue was purified by flash chromatography on silica, eluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89) and recrystallised from ethyl acetate/hexane to give the title compound (0.7 g) as a solid: m.p. 84°-85° C.; NMR (CDCl3) δ 8.3(2H,d); 6.86(4H,c); 6.72(2H,d); 4.12(2H,q); 4.0(2H,t); 3.47(4H,m); 3.20(4H,m); 2.5(2H,t); 2.1(2H,m); 1.26(3H,t); m/e 370(M+H)+ ; calculated for C21H27N3O3C, 68.3; H, 7.4; N, 11.4. Found: C, 68.1; H, 7.4; N, 11.1%.

Fuente