Reaction #2358518

Reaction equation

2-[3-Fluoro-5-(methylsulfonyl)phenoxy]ethanamine

propyl 4-methylbenzenesulfonate

potassium carbonate

→

title compound

Yield 44.0%

N-{2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl}-N-propylamine

Yield 44.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe reaction mixtures
2. 2
   Temperaturewere cooled to room temperature
3. 3
   Filtrationfiltrated
4. 4
   Otherwere evaporated
5. 5
   OtherPurification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1)

Procedure

2-[3-Fluoro-5-(methylsulfonyl)phenoxy]ethanamine (0.3 g, 1.26 mmol), propyl 4-methylbenzenesulfonate D2 (1.04 ml, 12.76 mmol) and potassium carbonate (0.35 g, 2.52 mmol) in acetonitrile (10 ml). The mixture was heated under microwave radiation at 120° C. for 45 min. The reaction mixtures were cooled to room temperature, filtrated and pooled before the volatiles were evaporated. Purification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (0.15 g, 44%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether. MS m/z (relative intensity, 70 eV) 277 (M+, 2), 248 (26), 138 (3), 94 (3), 74 (bp).

Source