HCID 67388622, compound → 1-Piperazinecarboxylic acid, 4-(4-piperidinylmethyl)-, 1,1-dimethylethyl ester

Participants

Reaction Steps

To a solution of benzyl 4-formylpiperidine-1-carboxylate (3 g) and tert-butyl piperazine-1-carboxylate (2.2 g) in dichloromethane (100 ml) was added sodium triacetoxyborohydride ((2.6 g). The resulting solution was stirred at room temperature for 18 hours and then washed with 2M sodium hydroxide (2×50 ml) and 2M hydrochloric acid (2×50 ml), dried over Magnesium sulphate, filtered and evaporated to afford tert-butyl 4-[(1-benzyloxycarbonyl-4-piperidyl)methyl]piperazine-1-carboxylate (4.9 g) as an oil. Tert-butyl 4-[(1-benzyloxycarbonyl-4-piperidyl)methyl]piperazine-1-carboxylate (4.9 g) was dissolved in ethanol and purged with argon. 20% Palladium hydroxide on carbon (500 mg) was added. The reaction mixture was purged with argon, evacuated and filled with hydrogen from a balloon. The reaction mixture was stirred at room temperature for 2 hours. A white solid precipitate formed. The reaction mixture was warmed to 40° C. and stirred at this temperature for a further 1 hour until the precipitate dissolved. The reaction mixture was allowed to cool to room temperature and stirred for a further 18 hours. The reaction mixture was purged with argon, filtered through celite and evaporated to afford tert-butyl 4-(4-piperidylmethyl)piperazine-1-carboxylate (3.2 g) as a solid. Mass spectrum: M+H+ 284

Provenance & Evidence