Potassium Carbonate → HCID 18923791, compound

Participants

Reaction Steps

The 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (3.0 g, 10 mmol), N-(2-chloroethyl)morpholine hydrochloride (1.9 g, 10 mmol), and powdered K2CO3 (7.1 g, 51 mmol) were stirred in 200 mL methyl ethyl ketone and refluxed 20 h. The reaction mixture was worked up and purified by prep. chromatography (EtOH/ CH2Cl2 gradient), triturated with Et2O/ pet. ether, filtered, and dried in vacuo to give 3.4 g (82% yield) of white solid: mp 66°-67° C.; 1H NMR (CDCl3) d 2.55-2.58 (m 4H, morpholine), 2.62 (s, 3H, pyr-CH3), 2.76-2.80 (t, 2H, J=6 Hz, NCH2), 3.72-3.75 (m, 4H, morpholine), 3.80 (s, 3H, ArOCH3), 4.06-4.10 (t, 2H, J=6 Hz, OCH2), 6.75-6.81 (m, 4H, ArH), 7.05-7.14 (m, 4H, ArH), 7.26-7.29 (m, 1H, ArH) 7.54-7.56 (d, 1H, J=8 Hz, ArH); MS(FD) 404(M+). Anal. Calcd for C25H28N2O3 : C, 74.23; H, 6.98; N, 6.93. Found: C, 74.50; H, 6.91; N, 7.05.

Provenance & Evidence