Potassium Carbonate → HCID 178426493, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl cis-4-aminocyclohexanecarbamate (1.27 g, 5.93 mmol) and 4-fluoro-3-nitrotoluene (0.92 g, 5.93 mmol) in DMF (20 mL) was added potassium carbonate (1.64 g, 11.88 mmol). The mixture was heated at 85° C. and stirred overnight. The mixture was cooled to room temperature and the solid was filtered. The filtrate was evaporated to dryness. The residue was extracted with ethyl acetate and brine. The organic layer was dried over sodium sulfate and solvents were evaporated. The resulting material was purified through flash column chromatography using hexanes and ethyl acetate (4:1) to give an orange colored solid as cis-[4-(4-methyl-2-nitro-phenylamino)-cyclohexyl]-carbamic acid tert-butyl ester (1.88 g). This material (1.80 g, 5.17 mmol) was suspended in a mixture of methanol (50 mL) and water (25 mL). To this suspension was added ammonium chloride (4.15 g, 77.6 mmol) and zinc dust (3.36 g, 51.6 mmol). The mixture was stirred at room temperature for 20 minutes and THF (20 mL) was added. The mixture was stirred an additional 1 hr during which the orange color disappeared. The mixture was filtered and rinsed with THF and ethyl acetate. The filtrate was extracted with brine and ethyl acetate. Solvents were evaporated to give cis-[4-(2-amino-4-methyl-phenylamino)-cyclohexyl]-carbamic acid tert-butyl ester (1.65 g). LC-MS showed a single peak, C18H29N3O2 (m/e) calcd 319.2260, obsd 320.3 (M+H).

Provenance & Evidence