Reaction #2358510

Reaction equation

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

sec-butylamine

→

title compound

Yield 70.4%

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

Yield 70.4%

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 sec-butylamine 1.37 ml, 13.46 mmol) in ethanol (5 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (342 mg, 70%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 166.5° C. MS m/z (relative intensity, 70 eV) 289 (M+, 1), 261 (25), 260 (bp), 86 (49), 70 (12).

Source