Potassium Carbonate → HCID 11731847, compound

Participants

Reaction Steps

The 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (4 g, 14 mmol), N-(2-chloroethyl)pyrrolidine hydrochloride (2.3 g, 14 mmol), and powdered K2CO3 (9.5 g, 68 mmol) were stirred in 250 mL methyl ethyl ketone and refluxed 18 h. The reaction mixture was worked up and purified by prep. chromatography (EtOH/ CH2Cl2 gradient), triturated with Et20, filtered, and dried in vacuo to give 3.7 g (71% yield) of white product: mp 63°-64° C.; 1H NMR (CDCl3) d 1.79-1.83 (comp, 4H, pyrrolidine), 2.60-2.64 (comp, 7H, Pyr-CH3 and pyrrolidine), 2.86-2.90 (t, 2H, J=6 Hz, NCH2), 3.81 (s, 3H, ArOCH3), 4.07-4.11 (t, 2H, J=6 Hz, OCH2), 6.78-6.82 (m, 4H, ArH), 7.06-7.30 (comp, 5H, ArH), 7.55-7.58 (d, 1H, J=8 Hz, ArH); MS(FD) 388(M+). Anal. Calcd for C25H28N202: C, 77.23; H, 7.26; N, 7.21. Found: C, 77.12; H, 7.48; N, 7.00.

Provenance & Evidence