Reaction #70545

Reaction equation

4-fluoro-2-methoxy-1-nitrobenzene

N,N-dimethylpiperidin-4-amine

N-ethyl-N-isopropylpropan-2-amine

→

title compound

1-(3-methoxy-4-nitrophenyl)-N,N-dimethylpiperidin-4-amine

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   workup.ADDITIONthe residue was mixed with water (60 mL)
3. 3
   Extractionextracted with CH2Cl2
4. 4
   OtherThe crude product was purified on a silica gel column
5. 5
   Washeluting with 7.5% methanol in CH2Cl2 saturated with NH3

Procedure

A solution of 4-fluoro-2-methoxy-1-nitrobenzene (1.711 g, 10 mmol), N,N-dimethylpiperidin-4-amine (1.410 g, 11.00 mmol) and N-ethyl-N-isopropylpropan-2-amine (3.48 mL, 20.00 mmol) in anhydrous N,N-dimethylformamide (25 mL) was stirred at 70° C. overnight. The mixture was concentrated and the residue was mixed with water (60 mL), adjusted to pH 12, then extracted with CH2Cl2. The crude product was purified on a silica gel column eluting with 7.5% methanol in CH2Cl2 saturated with NH3 to provide the title compound. (ESI+) m/e 280.1 (M+H)+.

Source