7-Chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one → 7-Chloro-5-(3-dimethylamino-propyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

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A mixture of 7-chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.102 g, 0.24 mmol) and 10% palladium-carbon (0.015 g) in ethanol (25 mL) was reduced under 45 p.s.i. hydrogen. Workup and silica gel column chromatography using 5:1 CHCl3-MeOH afforded 7-chloro-5-(3-dimethylamino-propyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.050 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.84 (m, 2H), 2.4 (s, 6H), 2.48 (t, 2H), 2.72 (t, 2H), 4.22 (s, 2H), 4.76 (s, 2H), 7.15-7.39 (m, 6H).

Provenance & Evidence