Hydrochloric Acid → HCID 15637642, compound

Participants

Reaction Steps

A mixture of the hydrochloride of 21c (250 mg, 0.67 mmol), potassium carbonate (463 mg, 3.35 mmol) and 4-iodobenzyl chloride (298 mg, 1.00 mmol) in absolute ethanol (25 mL) was refluxed for 16 h. When the mixture had cooled, salts were filtered off and the volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and the solution was successively washed with water (25 mL) and brine (25 mL). The organic layer was then dried (Na2SO4) and concentrated. The product was purified by chromatography (silica gel, hexanes/ethyl acetate: 50/50) and (13e) was obtained as a colorless oil (226 mg, 52%). The hydrochloride was prepared in a satd HCl/ether soln and recrystallized twice from 50% isopropyl alcohol-hexanes to yield a yellow powder; mp 256.3° C.; 1H NMR (CDCl3) δ1.56-2.18 (2 m, 8, 2 N--C H2 --C H2), 2.40-2.45 (d, 2H, Ar--C H2 --CH2, J=10.1 Hz), 2.51-2.60 (m, 2, C H2 --CHOH), 2.72-2.78 (m, 4, Ar--CH2 -C H2 --C H2), 2.84-2.97 (t, 2, N--C H2 --CH2 --CHOH, J=11.9 Hz), 3.05-3.50 (d, 2, CHN--C H2 --N, J=10.4 Hz), 3.40-3.55 (m, 4, C H--OH+Ar--CH2 --N+CHN), 3.81 (s, 1, OH), 7.22-7.02 (m, 4, arom.), 7.42-7.46 (d, 2, arom., J=7.7 Hz), 7.63-7.67 (d, 2, arom., J=8.2 Hz).

Provenance & Evidence