Water → HCID 21309138, compound

Participants

Reaction Conditions

Reaction Steps

Water (25 ml) and sulphuric acid (40 ml, concentrated) was added to a solution of 3-[1-(R)-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]aniline (3.8 g, 9.8 mmol prepared as described in International Patent specification No. WO95/17386) in 1,4-dioxane (50 ml) at RT. The mixture was heated at 90° C. for 1 h, cooled and concentrated in vacuo. The pH of the residue was adjusted to pH 8.0-8.5 by the addition of solid NaOH. The mixture was diluted with ethyl acetate (100 ml) and water (50 ml) and extracted with ethyl acetate (2×50 ml). The extract was washed with water (100 ml), brine (100 ml), dried (MgSO4), filtered and concentrated in vacuo to give a crude product which was washed with ethyl acetate to afford 3-[1-(R)-(3-hydroxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]aniline (Intermediate 1) as a pale yellow powder (2.84 g, 91%). (Found: C, 73.83; H, 6.44; N, 8.09. C20H20N2O2 +0.25 mol. eqv. of ethyl acetate requires C, 73.66; H, 6.48; N, 8.18%), δH (d4 -methanol) 3.3 (2H, d, J 8.0 Hz), 3.77 (3H, s), 4.06 (1H, t, J 8.0 Hz), 6.5 (1H, d, J 2.2 Hz), 6.53-6.78 (5H, m), 6.97 (1H, t, J 7.7 Hz), 7.13 (2H, d, J 5.8 Hz), and 8.25 (2H, d, J 5.6 Hz). m/z (ESI--MH+ 321 (25), 228 (100).

Provenance & Evidence