Triethylamine → HCID 25164129, compound

Participants

Reaction Steps

(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)amine (for example, as prepared for Intermediate 37) (248 mg, 0.7 mmol) was dissolved in DCM (5 ml), and treated with triethylamine (156 μl, 1.12 mmol), and ethanesulfonyl chloride (commercially available, for example, from Aldrich) (80 μl, 0.84 mmol). The mixture was stirred at room temperature for 2 h, then left to stand at room temperature overnight. The mixture was washed with saturated aqueous sodium hydrogen carbonate, passed through a hydrophobic frit and the organic solution was concentrated in vacuo. The residue was applied to a silica cartridge (20 g), eluting with DCM-ethanol-aqueous 0.88 s.g. ammonia (100:8:1). The relevant fractions were concentrated in vacuo to give the title compound (as the free base) as a yellow gum (167 mg). LCMS RT=2.66 min, ES+ve m/z 448 (M+H)+; 1H NMR δ (CD3OD) 8.72 (1H, dd, J=4, 1.5 Hz), 8.21 (1H, dd, J=8, 1.5 Hz), 7.48 (1H, dd, J=8, 4 Hz), 7.26 (1H, s), 7.10 (1H, s), 4.74-4.64 (1H, m), 3.10-2.92 (6H, m), 2.78 (2H, t, J=7.5 Hz), 2.50-2.38 (4H, m), 2.20-2.10 (2H, m), 2.08-1.95 (2H, m), 1.76-1.53 (6H, m), 1.47-1.36 (2H, m), 1.30 (3H, t, J=7 Hz), 0.97 (3H, t, J=7 Hz).

Provenance & Evidence