反应 #2302

反应方程式

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

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hours
2. 2
   其他Solvent was evaporated under reduced pressure
3. 3
   其他the residue was partitioned between ethyl acetate and water
4. 4
   洗涤The organic layer was washed with water
5. 5
   过滤filtered through phase
6. 6
   其他separating paper (Whatman 1PS)
7. 7
   其他evaporated
8. 8
   其他The residue was purified by flash chromatography on silica
9. 9
   洗涤eluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89)
10. 10
    其他recrystallised from ethyl acetate/hexane

实验过程

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%.

来源