Réaction #10274

Équation de réaction

ammonium hydroxide

4-benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

1-benzyl-3-(naphthalen-2-ylmethyl)piperazine

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter 75 min at room temperature the mixture was poured onto ice
2. 2
   AutreThe layers were separated
3. 3
   Extractionthe aqueous layer extracted with dichloromethane
4. 4
   SéchageThe combined organic layers were dried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 4-benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester (0.75 g) in dichloromethane (3 mL) was added dropwise trifluoroacetic acid (3 mL). After 75 min at room temperature the mixture was poured onto ice and made basic by the addition of ammonium hydroxide (25% solution). The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo to afford 1-benzyl-3-(naphthalen-2-ylmethyl)piperazine as an oil; 053 g (93%) MH+ 317, Rf 0.61 (CH2Cl2/MeOH/NH4OH 93/7/0.5), which was used as such.

Source