Reaction #2358513

Reaction equation

1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene

cyclobutylamine

→

title compound

Yield 82.9%

N-[2-(3-fluoro-5-methylsulfonyl-phenoxy)ethyl]cyclobutanamine

Yield 82.9%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherPreparation
2. 2
   OtherPurification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15)

Procedure

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and cyclobutylamine (1.17 ml, 13.46 mmol) in ethanol (4 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (400 mg, 82.7%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 202° C. MS m/z (relative intensity, 70 eV) 287 (M+, 0), 260 (33), 259 (91), 216 (bp), 215 (23), 56 (73).

Source