4-Nitrobenzyl chloride → 4-{[4-(Diphenylmethyl)-1-piperidinyl]methyl}benzenamine

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Reaction Steps

The basic primary amine of this invention can be prepared by heating 4-(diphenylmethyl)piperidine with 4-nitrobenzyl chloride in the presence of sodium carbonate, using ethanol and water as solvents, and contacting the resultant 1-[(4-nitrophenyl)methyl]-4-(diphenylmethyl)piperidine in tetrahydrofuran solution at 25° with hydrogen under approximately 0.1 atm of pressure, using 5% palladium-on-charcoal as catalyst. From 4-{[4-(diphenylmethyl)-1-piperidinyl]methyl}benzenamine thus or otherwise produced, on heating in acetic acid solution with an alkanoic acid anhydride, a corresponding basic N-alkanoyl amine of this invention can be prepared. And by heating a dichloromethane solution of 4-(diphenylmethyl)piperidine and 4-[(alkylamino)/(dialkylamino)]benzoic acid in the presence of N,N1 -methanetetraylbiscyclohexanamine, then heating the resultant amide with lithium tetrahydroaluminate(1-) in tetrahydrofuran, a corresponding basic N-alkyl or N,N-dialkyl amine of this invention can be prepared.

Provenance & Evidence