Dimethylformamide → 2-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide monofumarate

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Reaction Steps

Fumaric acid (1.86 g, 16 mmol) was added to 2-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide (6.7 g, 16 mmol). DMF (10 mL) and water (500 μL) were added to the mixture, and the solids were dissolved by warming on a steam bath. Isopropyl acetate (30 mL) was added gradually while heating on a steam bath. The heat was removed, and material oiled out. The mother liquors were decanted. About 100 mL MTBE were added to the residual oil, which was stirred for several hours until the mixture was a uniform slurry. A solid was collected and washed with MTBE. The solid was harvested and dried by vacuum filtration on a Büchner funnel. NMR shows a 1.9:1 ratio of fumaric acid to base. The solid was air-dried over night.

Provenance & Evidence