Reaction #160747

Reaction equation

diethyl 4-chloropiperidin-3-ylphosphoramidate

4-chloro-3-nitropyridine

DIEA

→

diethyl 4-chloro-1-(3-nitropyridin-4-yl)piperidin-3-ylphosphoramidate

Yield 69.0%

Solvents

isopropyl alcohol

Conditions

Workup

1. 1
   Otherquenched with water
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe organics were dried
4. 4
   Concentrationconcentrated under vacuo
5. 5
   OtherThe crude was purified via ISCO (ethyl acetate and hexanes

Procedure

To a solution of diethyl 4-chloropiperidin-3-ylphosphoramidate (1.0 equiv.) in isopropyl alcohol (0.1M) was added 4-chloro-3-nitropyridine (2.0 equiv.) and DIEA (1.1 equiv.). The reaction was heated to 70° C. for 18 h, then quenched with water and extracted with ethyl acetate. The organics were dried and concentrated under vacuo. The crude was purified via ISCO (ethyl acetate and hexanes then 10% methanol in DCM) to yield diethyl 4-chloro-1-(3-nitropyridin-4-yl)piperidin-3-ylphosphoramidate in 69% yield. LCMS (m/z): 393.1 (MH+), Rt=2.01 min.

Source