Réaction #325084

Équation de réaction

2-(2-(chloromethyl)phenyl)acetic acid

morpholine

→

2-(2-(Morpholinomethyl)phenyl)acetic acid

Rendement 87.4%

Solvants

ethyl acetate

THF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with H2O (2×)
2. 2
   Autrethe residue was purified by silica gel chromatography (Biotage/0-10% methanol-CH2Cl2)

Mode opératoire

To a suspension of 2-(2-(chloromethyl)phenyl)acetic acid (2.00 g, 10.8 mmol) in THF (20 mL) was added morpholine (1.89 g, 21.7 mmol) and the solution was stirred at room temperature for 3 hours. The reaction mixture was then diluted with ethyl acetate and extracted with H2O (2×). The aqueous phase was lyophilized and the residue was purified by silica gel chromatography (Biotage/0-10% methanol-CH2Cl2) to give the title compound 2-(2-(Morpholinomethyl)phenyl)acetic acid as a colorless solid (2.22 g, 87%). 1HNMR (400 MHz, CD3OD) δ 7.37-7.44 (m, 3H), 7.29-7.33 (m, 1H), 4.24 (s, 2H), 3.83 (br s, 4H), 3.68 (s, 2H), 3.14 (br s, 4H). LCMS: Anal. Calcd. for C13H12NO3: 235. found: 236 (M+H)+.

Source