3-Hydroxybenzaldehyde → 1-(3-Hydroxybenzyl)piperidine

Participants

Reaction Steps

First, 3-piperidinomethylphenol is synthesized from 3-hydroxybenzaldehyde and piperidine. The 3-piperidinomethylphenol is then reacted with 3-chloropropylamine to produce N-[3-(3-aminopropoxy)benzyl]piperidine, which is reacted with acetoxyacetyl chloride to obtain N-[3-(3-piperidinomethylphenoxy)propyl]hydroxyacetamide. Separately, tranexamic acid and carbobenzoxy chloride are reacted to produce N-carbobenzoxyaminomethylhexanecarboxy chloride. The two compounds thus obtained are then reacted first to afford N-{3-[3-(1-piperidinomethyl)phenoxy]propyl}-2-(N-carbobenzoxy-aminomethylhexanecarboxy)acetamide. This compound is then reduced into 2-(aminomethylcyclohexanecarboxy)-N-(3-[3-(piperidinomethyl)phenoxy]propyl}acetamide.

Provenance & Evidence