4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → N-[(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1H-indol-3-yl)propionamide

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Reaction Steps

The more polar diastereomer of 2-amino-N-(4-dimethylamino-4-phenylcyclohexyl)-acetamide (159 mg, 0.57 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (239 mg, 0.86 mmole) were added to a solution of indol-3-yl-propionic acid (109 mg, 0.57 mmole) in MeOH and stirred for 24 h at room temperature. Working up was performed by removing MeOH by distillation. The batch was re-dissolved with water, adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate. The organic phase was dried with Na2SO4 and evaporated. The more polar amide was obtained as a colorless oil in a yield of 257 mg (100%).

Provenance & Evidence