Reaction #2358512

Reaction equation

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

tert-amylamine

→

title compound

Yield 76.3%

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

Yield 76.3%

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 tert-amylamine (1.61 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 (389 mg, 76.2%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 190.2° C. MS m/z (relative intensity, 70 eV) 303 (M+, 0), 288 (21), 276 (10), 275 (41), 274 (bp), 84 (10).

Source