反応 #2302

反応方程式

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

溶媒

DMF

反応条件

後処理

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

実験手順

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%.

出典