6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → N-(2-tert-butoxybenzyl)-6-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine

Participants

Reaction Steps

The same procedure as described for compound 11 was applied to starting material 10 (0.4 g, 0.92 mmol) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (0.267 g, 1.38 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 4.5% methanolic NH3 (7 M NH3 in methanol/94.5% CH2Cl2. The product was isolated as pale yellow oil (99%). 1H NMR (CDCl3) δ 8.463 (dt, 1H, Ar), 7.574 (m, 3H, Ar), 7.082 (m, 2H, Ar), 6.996 (m, 2H, Ar), 6.552 (s, 1H, Ar), 6.486 (s, 1H, Ar), 3.797 (s, 3H, —OCH3), 3.792 (s, 3H, —OCH3), 3.723 (s, 2H, —CH2—), 3.646, (s, 2H, —CH2—), 3.504 (s, 2H, —CH2—), 2.784 (t, 2H, —CH2—), 2.655 (t, 2H, —CH2—), 2.430 (m, 4H, —CH2—CH2—), 1.521 (m, 4H, —CH2—CH2—), 1.333 (s, 9H, —C(CH3)3—), 1.264 (m, 4H, —CH2—CH2—). Mass Spec=546.37 (M+H)+.

Provenance & Evidence