Triethylamine → N-Methoxy-N-methyl-4-fluoro-benzenepropanamide

Temperature

0 °C

A suspension of 10.00 g (59.46 mmol) of 3-(4-fluorophenyl)propionic acid, 12.54 g (65.41 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 6.381 g (65.41 mmol) of N,O-dimethylhydroxylamine hydrochloride in 300 mL of CH2Cl2 was cooled to 0° C. and treated with 18.23 mL (13.23 grams, 130.8 mmol) of triethylamine. The mixture was stirred for 16 h with slow warming to rt. The mixture was concentrated, and the residue was partitioned between 300 mL of EtOAc and 200 mL of aqueous 1 N hydrochloric acid solution. The separated organic layer was washed with aqueous 1 N hydrochloric acid solution (1×100 mL), saturated aqueous sodium hydrogencarbonate solution (2×200 mL), brine (1×100 mL), dried (Na2SO4), and evaporated to give 9.56 g (76% yield) of the title compound as an oil. 1H NMR (CDCl3) d 2.70(2H, t, J=8 Hz), 2.91 (2H, t, J=8 Hz), 3.15 (3H, s), 3.59 (3H, s), 6.92-6.97 (2H, m), 7.15-7.19 (2H, m). APCI MS (m/e) 212 (M++1).

1. temperaturewith slow warming to rt
2. concentrationThe mixture was concentrated
3. customthe residue was partitioned between 300 mL of EtOAc and 200 mL of aqueous 1 N hydrochloric acid solution
4. washThe separated organic layer was washed with aqueous 1 N hydrochloric acid solution (1×100 mL), saturated aqueous sodium hydrogencarbonate solution (2×200 mL), brine (1×100 mL)
5. dry with materialdried (Na2SO4)
6. customevaporated

ORD record

ord-94c0784ee27c40a8a64e3a51750f579e

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380218B1