Reaktion #2507888

Reaktionsgleichung

DMF

2-methoxy-5-nitrophenol

1-(2-chloroethyl)pyrrolidine hydrochloride

K2CO3

→

4-methoxy-3-(2-(pyrrolidin-1-yl)ethoxy)benzenamine

Ausbeute 87.0%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (3×20 mL)
2. 2
   WaschenThe combined EtOAc layers were washed brine
3. 3
   Trocknendried over MgSO4
4. 4
   EinengenAfter concentration under vacuum
5. 5
   Sonstigethe resulting residue was chromatographed on silica gel
6. 6
   WaschenGradient elution CH2Cl2 to 10% MeOH/CH2Cl2
7. 7
   Wascheneluted N-(2-(2-methoxy-5-nitrophenoxy)ethyl)pyrrolidine (507 mg) as a light orange solid

Vorschrift

A stirred DMF suspension (5 mL) of 2-methoxy-5-nitrophenol (0.5 g, 2.96 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (0.75 g (4.43 mmol) and K2CO3 (1.02 g, 7.4 mmol) was heated at 80° C. for 2 hr. After cooling to RT, the reaction was diluted with 20 mL of H2O and extracted with EtOAc (3×20 mL). The combined EtOAc layers were washed brine and dried over MgSO4. After concentration under vacuum, the resulting residue was chromatographed on silica gel. Gradient elution CH2Cl2 to 10% MeOH/CH2Cl2 eluted N-(2-(2-methoxy-5-nitrophenoxy)ethyl)pyrrolidine (507 mg) as a light orange solid. Subsequent conversion of the aryl nitro substituent to the title aryl amine was accomplished in 87% yield following the procedure described in step C of Example 6. MS (ESI) 237 (M+H)+.

Quelle