4-Chloroisatoic anhydride → 2-amino-4-chloro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 7-chloro-1,2-dihydro-4H-3,1-benzoxazin-2,4-dione (prepared by cyclization of N-benzyloxycarbonyl-4-chloroanthranilic acid with phosphorus tribromide) (1.0 g, 5.06 mmol) in DMF (18 ml) was added 4-dimethylaminopyridine (62 mg). After 5 mins of agitation at room temperature, 4-aminomethyl-1-diphenylmethylpiperidine (1.56 g, 5.56 mmol) was added to the solution and stirred for 5 hours. The reaction mixture was diluted with AcOEt, washed twice with H2O, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 2-amino-4-chloro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 892 mg (41%): mp 161°-162° C.

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