Sodium hydride → HCID 18353762, compound

Participants

Reaction Steps

A solution of 3-(3,4-dichlorobenzylamino)propanol (47 mg, 0.2 mmol) in dry THF (0.5 ml) was added to a suspension of sodium hydride (60% dispersion in oil, 8.0 mg, 0.2 mmol) at room temperature under an argon atmosphere. After 10 min the mixture was heater to reflux for a further 20 min. A solution of 2-chloro-4-(4-methoxybenzyloxy)quinoline (62 mg, 0.2 mmol) in dry THF (0.5 ml) was added and reflux continued under an argon atmosphere for a further 30 min. The solvent was evaporated, the residue dissolved in toluene and applied to a column of Kieselgel 60. Elution with a mixture of 70:29:1 ethyl acetate:hexane:2M methanolic ammonia afforded the title compound as a colourless oil (17 mg, 17%); δH (CDCl3) 1.6 (1H, br. s.), 1.97-2.12 (2H, m), 2.79 (2H, t, J=6.8 Hz), 3.76 (2H, s), 3.84 (3H, s), 4.57 (2H, t, J=6.2 Hz), 5.14 (2H, s), 6.27 (2H, s), 6.96 (2H, d, J=8.6 Hz), 7.13-7.44 (6H, m), 7.58 (1H, dt, J=1.1, 7.1 Hz), 7.70 (1H, d, J=8.2 Hz), 8.09 (1H, d, J=8.2 Hz); MS (ES+) 497 (MH+, 50%), 216 (100).

Provenance & Evidence