3-Iodoaniline → 1-(4-(3-Aminophenyl)-3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

Participants

Reaction Steps

A solution of 1-(3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine (263 mg, 1.00 mmol), 3-iodoaniline (208 mg, 0.950 mmol) and tetrakis(triphenylphosphine) palladium (0) (46 mg) in n-butylamine (5 mL) is allowed to reflux for 15 hr. The solvent is evaporated in vacuo to give a residue, which is purified by flash chromatography giving the product as an off white solid (231 mg, 69%): mp 139-140° C.; 1H NMR (CDCl3) 1.71 (m, 3 H), 2.12 (m, 2 H), 2.56 (m, 4 H), 2.73 (m, 2 H), 2.84 (m, 2 H), 3.60 (bs, 2 H), 6.59 (d, J=7.5 Hz, 1 H), 6.72 (s, 1 H), 6.79 (d, J=7.5 Hz, 1 H), 7.07 (dd, J1=J2=7.5 Hz, 1 H), 7.33 (d, J=9.7 Hz, 2 H), 7.46 (d, J=9.7 Hz, 2 H).

Provenance & Evidence