Reaction #78240

Reaction equation

aluminum oxide

diethyl ether

1-benzylpiperidin-4-spiro-2′-oxirane

4-butoxy-N-methylaniline

→

titled compound

Yield 75.5%

1-benzyl-4-[N-(4-n-butoxyphenyl)-N-methylaminomethyl]piperidin-4-ol

Yield 75.5%

Solvents

Methanol

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 2 hours
2. 2
   FiltrationThe reaction solution was filtered
3. 3
   Concentrationthe filtrate was concentrated under reduced pressure
4. 4
   OtherThe residue obtained
5. 5
   Otherwas purified by silica gel column chromatography (elution solvent; ethyl acetate)

Procedure

Activated neutral aluminum oxide 90 (activity I, made by Merck Co.) (5 g) was added to a diethyl ether solution (10 mL) of 1-benzylpiperidin-4-spiro-2′-oxirane (0.50 g) and 4-butoxy-N-methylaniline (0.53 g) and stirred at room temperature overnight. Methanol (20 mL) was added to the reaction solution and stirred at room temperature for 2 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution solvent; ethyl acetate) to obtain the titled compound (0.71 g).

Source