4-Phenylcyclohexanone → m-(Trifluoromethyl)benzamide

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Reaction Steps

N-(2-(cis-4-amino-cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (60 mg, 0.158 mmol, 1 eq), 4-phenylcyclohexanone (28 mg, 0.158 mmol, 1 eq) and sodium triacetoxyborohydride (67 mg, 0.316 mmol, 2 eq) were stirred in 2% acetic acid/methylene chloride (10 mL) at room temperature for 20 hours. Worked up by adding saturated sodium bicarbonate (10 mL). Stirred 10 minutes then extracted 3 times with methylene chloride (10 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 100% ethyl acetate to 4:1 methylene chloride/methanol to give N-(2-oxo-2-(cis-4-(cis- and trans-4-phenylcyclohexylamino)cyclohexylamino)ethyl)-3-(trifluoromethyl)benzamide (42 mg) as an off-white amorphous solid. MS found: (M+H)+=502.33.

Provenance & Evidence