Ammonia → 1-(3-Chlorobenzylamino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

Participants

Reaction Steps

With the exclusion of moisture, 1.6 ml (13.1 mmol) of 3-chlorobenzylamine and 800 mg (3.14 mmol) of 1-chloro-4-(pyridin-4-ylmethyl)-isoquinoline (Example 1e) are stirred for 2 hours at 150° C. The mixture is suspended in ethyl acetate, 1 ml of concentrated ammonia solution is added, washing with water and brine is carried out, and the organic phase is dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; ethyl acetate) yields the title compound: m.p. 141-142° C.; 1H NMR (DMSO-d6) 8.39 (d, 2H), 8.31 (d, 1H), 8.03 (t, HN), 7.82 (s, 1H), 7.69 (d, 1H), 7.61 (t, 1H), 7.50 (t, 1H), 7.40 (s, 1H), 7.33 (m, 2H), 7.26 (m, 1H), 7.20 (d, 2H), 4.73 (d, 2H), 4.14 (s, 2H); FAB-MS: (M+H)+=360; Anal. calc. (C22H18N3Cl) C 73.43%, H 5.04%, N 11.68%, Cl 9.85%; found C 73.2%, H 5.1%, N 11.6%, Cl 9.9%.

Provenance & Evidence