4-(3,3,3-Triphenylpropoxy)benzyl chloride → N,N,N-Trimethyl-[4-(3,3,3-triphenylpropoxy)phenyl]methylammonium chloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(3,3,3-triphenylpropoxy)benzyl chloride, prepared in example 28, (413 mg, 1.0 mmol) in commercial 33% trimethylamine-ethanol solution was sealed in a screw-topped culture tube and was heated to 80° C. for 24 hr. The mixture was cooled and the solvent evaporated, and the residue recrystallized from isopropanol-ethyl acetate to provide the title compound as a hydrate, a white powder, mp 224°-225° C. (dec). 1H NMR (CDCl3) δ 7.43 (d, J=8.7 Hz, 2H) 7.15-7.35 (m, 15H), 6.71 (d, J=8.7 Hz, 2H), 4.82 (s, 2H), 3.73 (t, J=7.7 Hz, 2H), 3.31 (s, 9H), 3.13 (t, J=7.7 Hz, 2H). Anal. calcd. for C31H34NO·C·1.5H2O: C, 74.60; H, 7.47; N, 2.81; Cl, 7.10. Found: C, 74.99; H, 7.49; N, 2.83; Cl, 7.07.

Provenance & Evidence