Isoquinoline → (3-{[1-(3-Methoxy-phenyl)-ethyl]-methyl-amino}-propyl)-carbamic acid ter-butyl ester

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Reaction Steps

A solution of [1-(3-methoxy-phenyl)-ethyl]-methyl-amine (IV) (Grethe, Guenter; Lee, Hsi Lin; Uskokovic, Milan; Brossi, Arnold. Syntheses in the isoquinoline series. Synthesis of 2,3-dihydro-4(1H)-isoquinolones. Journal of Organic Chemistr 1968, 33, 491-494) (320 mg, 1.9 mmol), (3-chloro-propyl)-carbamic acid tert-butylic ester (370 mg, 1.9 mmol), K2CO3 (260 mg, 1.9 mmol) and a catalytic quantity of KI in DMF (5 mL) was stirred under reflux conditions for 24 h. Evaporation of the solvent afforded a residue which was purified by gravity column. Elution with CHCl3/MeOH/aqueous 30% ammonia solution (9:1:0.005) afforded V as an oil: 40% yield, 1H NMR (200 MHz, CDCl3) δ 7.20 (t, J=8.0 Hz, 1H); 6.74-6.95 (m, 3H), 5.38 (br s, 1H, exchangeable with D2O), 3.80 (s, 3H); 3.50 (q, J=7.0 Hz, 1H), 3.13 (q, J=6.2 Hz, 2H), 2.30-2.52 (m, 2H), 2.19 (s, 3H), 1.54-1.68 (m, 2H), 1.44 (s, 9H), 1.35 (d, J=6.6 Hz, 3).

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