Reaction Steps
The 2-(4-hydroxyphenyl)-3,6-bis(4-methoxyphenyl)pyridine (2.3 g, 6 mmol), N-(2-chloroethyl)pyrrolidine hydrochloride (1.1 g, 6 mmol), and powdered K2CO3 (4.1 g, 30 mmol) were stirred in 250 mL methyl ethyl ketone and refluxed 18 h. The TLC (EtOH/ CH2Cl2, 1:4) of the reaction mixture indicated some starting material remained, so more N-(2-chloroethyl)pyrrolidine hydrochloride (0.3 g, 1.6 mmol) and K2 CO3 (2 g, 15 mmol) were added and reaction mixture refluxed an additional 18 h. The reaction mixture was worked up, concentrated, and the residue was dissolved in 25 mL MeOH, treated with 5 mL HCl/ MeOH at 0° C., and concentrated. The residue was recrystallised from MeOH/ Et2O to give 1.8 g (58% yield) of product as the HCl salt: mp 230°-231° C.; 1H NMR (CDCl3) d 1.61 (bs, 2H, pyrrolidine), 2.10-2.26 (comp, 4H, pyrrolidine), 2.90-3.10 (bs, 2H, pyrrolidine), 3.48 (bs, 2H, NCH2), 3.84 (s, 3H, ArOCH3), 3.88 (s, 3H, ArOCH3), 4.10-4.14 (m, 2H, OCH2), 6.78-6.81 (d, 2H, J=9 Hz, ArH), 6.86-6.89 (d, 2H, J=9 Hz, ArH), 7.00-7.03 (d, 2H, J=9 Hz, ArH), 7.14-7.16 (d, 2H, J=9 Hz, ArH), 7.44-7.46 (d, 2H, J=9 Hz, ArH), 7.66-7.73 (m, 2H, ArH), 8.07-8.10 (d, 2H, J=9 Hz, ArH); MS(FD) 480(M+). Anal. Calcd for C31H32N2O3HCl: C, 72.01; H, 6.43; N, 5.42. Found: C, 72.02; H, 6.65; N, 5.24.
