Acetic Acid → 1-Methyl-4-(4-nitrobenzyl)piperazine

Participants

Reaction Steps

p-Nitrobenzaldehyde (2.50 g, 16.5 mmol) and piperazine, 1-methyl- (3.31 g, 33.1 mmol) were dissolved in Acetic acid (2.0 mL, 35 mmol) and Methylene chloride (100 mL, 2000 mmol) and the solution was allowed to stir at room temperature for approximately 15 minutes. Sodium triacetoxyborohydride (5.26 g, 24.8 mmol) was then added and the reaction was allowed to stir overnight. The reaction mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent). Combined fractions were reduced and dried under vacuum to afford 3.77 g of 1-Methyl-4-(4-nitro-benzyl)-piperazine. (M+H)=236.6.

Provenance & Evidence