4-Nitrophenol → 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Participants

Reaction Steps

A stirred DMF suspension (5 mL) of 4-nitrophenol (0.5 g, 3.6 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (0.92 (5.4 mmol) and K2CO3 (1.24 g, 9 mmol) was heated at 80 for 3 hr. After cooling to RT, the reaction was diluted with H2O and extracted 3× with EtOAc. The combined EtOAc layers were washed 2× with H2O and dried over MgSO4. After concentration under vacuum, the resulting residue was chromatographed on silica gel. Gradient elution CH2Cl2 to 10% MeOH/CH2Cl2 eluted the 1-(2-(4-nitrophenoxy)ethyl)pyrrolidine (560 mg) as an orange oil. Further purification employing reverse phase chromatography (MeOH/H2O/0.1% TFA) yielded 413 mg of a yellow oil. Subsequent conversion of the aryl nitro substituent to the title aryl amine was accomplished following the procedure described in Example 6 step C. MS (ESI) 207 (M+H)+.

Provenance & Evidence