Potassium Carbonate → 6-bromo-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

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Reaction Steps

Compound 10 was synthesized with 9 (2 g, 8.84 mmol), using 1,6-dibromohexane (30 g, 130 mmol) and K2CO3 (1.22 g, 8.84 mmol) following a procedure analogous to that described for 2. Purification was carried out on a silica gel TLC plate that was developed in with a 1% methanolic NH3 (7 M NH3 in methanol/99% CH2Cl2. The product was isolated as pale yellow oil (73%).δ 1H NMR (CDCl3) δ 8.491 (dd, 1H, Ar), 7.630 (t, 1H, Ar), 7.565 (t, 2H, Ar), 7.120 (t, 2H, Ar), 7.020 (t, 2H, Ar), 3.740 (s, 2H, —CH2—), 3.660 (s, 2H, —CH2—), 3.334 (t, 2H, —CH2—), 2.452 (s, 2H, —CH2—), 1.787 (p, 2H, —CH2—), 1.516 (m, 2H, —CH2—), 1.354 (s, 9H, —C(CH3)3), 1.269 (m, 4H). Mass Spec.=435.18 (M+H)+.

Provenance & Evidence