Hydrochloric Acid → HCID 9889249, compound

Participants

Reaction Conditions

Reaction Steps

The 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-phenylpyridine as the HCl salt (1.9 g, 3.9 mmol) was slurried with 50 mL of DCE in a screw cap flask, cooled to 0° C., and stirred while the BCl3 (2.7 mL at 0° C., 32 mmol) in 5 mL DCE was added and the reaction flask sealed. After 2 h, TLC (EtOH/ CH2Cl2, 1:4) indicated that starting material remained, so an additional 1.7 mL of BCl3 (20 mmol) was added and reaction mixture stirred for 18 h. The reaction mixture was carefully quenched with 25 mL MeOH at 0° C., poured in 150 mL of aqueous NaHCO3, and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 extracts were combined, washed with brine, dried (Na2SO4), concentrated, and recrystallised from EtOH to give 1.35 g (79 % yield) of product: mp 176°-178° C.; 1H NMR (CDCl3) d 1.86 (bs, 4H, pyrrolidine), 2.73(bs, 4H, pyrrolidine), 2.97-3.01 (t, 2H, J=5 Hz, CH2N), 4.12-4.16 (t, 2H, J=5 Hz, OCH2), 6.64-6.67 (m, 4H, ArH), 6.98-7.01 (d, 2H, J=8 Hz, ArH), 7.38-7.50 (m, 5H, ArH), 7.67 (s, 2H, ArH), 8.10-8.12 (d, 2H, J=8 Hz, ArH); MS(FD) 436 (M+). Anal. Calcd for C29H28N2O2 : C, 79.79; H, 6.46; N, 6.42. Found: C, 80.01; H, 6.55; N, 6.54.

Provenance & Evidence