반응 #2302

반응 방정식

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

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hours
2. 2
   기타Solvent was evaporated under reduced pressure
3. 3
   기타the residue was partitioned between ethyl acetate and water
4. 4
   세척The organic layer was washed with water
5. 5
   여과filtered through phase
6. 6
   기타separating paper (Whatman 1PS)
7. 7
   기타evaporated
8. 8
   기타The residue was purified by flash chromatography on silica
9. 9
   세척eluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89)
10. 10
    기타recrystallised from ethyl acetate/hexane

실험 절차

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%.

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