反应详情

A stirred suspension of 4-[3-(1-piperidinylmethyl)phenoxy]butanoic acid (4.0 g) in methylene chloride (100 ml) and dimethylformamide (24 drops) was treated with thionyl chloride (5.16 g). The solution was stirred at room temperature for 18 h and evaporated in vacuo, to give a pale yellow solid which was dissolved in methylene chloride (100 ml) and treated with 5-amino-1,3-dimethyl-1,2,4-triazole (1.61 g). The reaction mixture was stirred at room temperature for 24 h and evaporated in vacuo. The residue was dissolved in aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were dried and evaporated to give a brown oil which was dissolved in tetrahydrofuran (500 ml), treated with lithium aluminium hydride (3.04 g), stirred at room temperature for 18 h and refluxed for 3 h. The cooled reaction mixture was quenched with water (300 ml) and extracted with ethyl acetate. The combined extracts were washed with brine, dried and evaporated in vacuo to give an oil which was distilled to give the title compound (1.7 g) as a pale yellow oil, b.p. 230°/0.06 mm.

1. customevaporated in vacuo
2. customto give a pale yellow solid which
3. stirringThe reaction mixture was stirred at room temperature for 24 h
4. customevaporated in vacuo
5. dissolutionThe residue was dissolved in aqueous sodium bicarbonate solution
6. extractionextracted with ethyl acetate
7. customThe organic extracts were dried
8. customevaporated
9. customto give a brown oil which
10. stirringstirred at room temperature for 18 h
11. temperaturerefluxed for 3 h
12. customThe cooled reaction mixture
13. customwas quenched with water (300 ml)
14. extractionextracted with ethyl acetate
15. washThe combined extracts were washed with brine
16. customdried
17. customevaporated in vacuo
18. customto give an oil which
19. distillationwas distilled