Piperidine → Methyl 2-nitro-5-(piperidin-1-ylmethyl)benzoate

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Reaction Steps

Methyl 5-(bromomethyl)-2-nitrobenzoate was added to a DMF suspension of potassium carbonate and piperidine, followed by stirring at room temperature to obtain methyl 2-nitro-5-(piperidin-1-ylmethyl)benzoate (Dat, ES: 279). This compound was dissolved in acetic acid, iron powder was added thereto, followed by stirring at 60° C. to obtain methyl 2-amino-5-(piperidin-1-ylmethyl)benzoate (Dat, F: 249). Cyclohexanone and sodium triacetoxyborohydride were added to an acetic acid solution of this compound, followed by stirring at room temperature. By post-treating the reaction liquid, methyl 2-(cyclohexylamino)-5-(piperidin-1-ylmethyl)benzoate was obtained.

Provenance & Evidence