Mechlorethamine → 7-Methyl-5-(4-methyl-piperazin-1-ylmethyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

In sealed vial, a mixture of 5-aminomethyl-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.104 g, 0.3 mmol), bis(2-chloro-ethyl)-methyl-amine (0.077 g, 0.4 mmol), and K2CO3 (0.083 g, 0.6 mmol) in DMF (3 mL) was stirred at 110° C. for 16 h. After this time, the GC-MS of the reaction mixture indicated the completion of reaction. The reaction was cooled to ambient temperature and the solids removed by filtration. The filtrate was concentrated. Silica gel column chromatography of the resulting material using 5:1 CHCl3-MeOH afforded 7-methyl-5-(4-methyl-piperazin-1-ylmethyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.040 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.24 (s, 3H), 2.34-2.52 (m, 8H), 2.74 (s, 3H), 3.49 (s, 2H), 4.20 (s, 2H), 4.76 (s, 2H), 7.15-7.37 (m, 6H). GC-MS: m/z 433 (M)+.

Provenance & Evidence