Ethyl Acetate → 4-n-Butyl-1-[4-(2ethoxyphenyl)-4-oxo-1-butyl]piperidine

Temperatur

40 °C

In a 10 mL oven-dried flask was added Mg turnings (94 mg, 3.8 mmol) which was activated by the use of a heat-gun under vacuum. Under inert atmosphere was added a suspension of 1-ethoxy-2-iodobenzene (0.71 g, 2.9 mmol) in Et2O (3 mL) and the reaction mixture was allowed to reflux for 3 hours. Compound 4 (0.40 g, 1.9 mmol) dissolved in CH2Cl2 (3 mL) was added and the mixture was stirred at 40° C. for additional 3 hours. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and left stirring overnight at room temperature, followed by addition of NaOH (20 mL, 2 M) until basic conditions. The reaction mixture was extrated with ethyl acetate (3×50 mL) ) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the combined organic phases were dried (MgSO4) and evaporated to dryness to produce 0.60 g of crude 18. The crude product was subjected to CC [eluent:Tol:EtOAc (1:1)] to give pure 18 (0.32 g, 34%); LC-MS [M+H]+ 331 (cald. 331.5).

1. customIn a 10 mL oven-dried flask
2. temperaturea heat-gun under vacuum
3. additionUnder inert atmosphere was added
4. temperatureto reflux for 3 hours
5. additionwas added
6. customThe reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M)
7. waitleft
8. stirringstirring overnight at room temperature
9. additionfollowed by addition of NaOH (20 mL, 2 M) until basic conditions
10. washare washed with brine (10 mL) and NaOH (10 mL, 2 M)
11. dry with materialthe combined organic phases were dried (MgSO4)
12. customevaporated to dryness
13. customto produce 0.60 g of crude 18

ORD-Eintrag

ord-b685cb8ea2eb4b07b9d171232fefc84c

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06528529B1