Dimethylamine → HCID 11611371, compound

Participants

Reaction Steps

Dimethylamine (1.05 ml, 2.1 mmol), acetic acid (0.81 ml), and formaldehyde (0.042 ml) were added to a solution of 2-(1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (600 mg, 1.71 mmol) prepared in Example 44 in ethanol (5 ml). The resulting mixture was refluxed under stirring overnight and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting compound (300 mg, 0.73 mmol) was dissolved in ethanol (2 ml). Iodomethane (0.091 ml, 0.46 mmol) was added to the solution, which was stirred overnight at room temperature. The resulting white product (100 mg, 0.18 mmol) was dissolved in N,N-dimethylformamide (3 ml). Sodium cyanide (34 mg, 0.72 mmol) was added to the solution, which was then stirred for 5 hours at 100° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography, dissolved in ether, and then saturated with hydrochloric acid gas to give the titled compound as a white solid (25 mg, 34.0%).

Provenance & Evidence