8-Phenyloctan-1-amine → N-(8-Phenyloctyl)4-(2-hydroxyethoxy)-5-(3-chloro-4-fluorophenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a flamed dried round bottom flask charged with 8-phenyloctylamine (688 mg, 3.35 mmol, 6.68 μL) in 5 mL THF at −78° C. was added n-BuLi (2.2 mL, 4.4 mmol) as a solution in hexanes. The solution was stirred at −78° C. for 30 min then stirred at room temperature for 15 min. The solution was cooled back down to −40° C. and a cooled (-40° C.) solution of 3-bromo-4-(2-hydroxyethoxy)-5-(3-chloro-4-fluorophenyl)benzoic acid ethyl ester (400 mg, 0.957 mmol) in 10 mL THF via cannula. After the addition was completed, the reaction was warmed up to room temperature, stirred for 10 min, then worked up as in Step 2 of Example 135. The crude yellow oil that was obtained was dissolved in 1:1 EtOAc/Hexanes and filtered through a pad of silica gel with the same solvent system to yield 200 mg, 43% of the amide as a yellow oil. 1H NMR (CDCl3) 1.25-1.40 (m, 2H); 1.54-1.65 (m, 2H); 1.80 (bs, 1H); 2.57 (t, J=8.18, Hz, 2H); 3.41 (q, J=6.54 Hz, 2H); 3.90 (t, J=6.13, 2H); 4.12 (t, J=6.13 Hz, 2H); 6.07 (m, 1H); 6.99 (d, J=8.13 Hz, 1H); 7.08-7.18 (m, 3H); 7.20-7.27 (m, 2H); 7.33-7.40 (m, 1H); 7.56 (dd, J=6.54 Hz, 3.27 Hz, 1H); 7.65-7.69 (m, 1H); 7.73 (dd, J=8.13 Hz, 2.58 Hz, 1H).

Provenance & Evidence