Réaction #68858

Équation de réaction

NaOH

NaB(OAc)3H

HCl

piperazine-1-carboxylic acid phenylamide

3-hydroxybenzaldehyde

→

title compound

Rendement 82.4%

4-(3-Hydroxy-benzyl)-piperazine-1-carboxylic acid phenylamide

Rendement 82.4%

Solvants

DCM

acetic acid

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous phase was extracted with DCM (200 mL)
2. 2
   SéchageThe combined organic layers were dried (MgSO4)
3. 3
   Concentrationconcentrated

Mode opératoire

To a solution of piperazine-1-carboxylic acid phenylamide (2.0 g) and 3-hydroxybenzaldehyde (3.0 g) in DCM (200 mL) was added acetic acid (1.1 mL) followed by portion-wise addition of NaB(OAc)3H (6.0 g). The reaction mixture was stirred overnight. A solution of 10% aq. NaOH (30 mL) was added until the pH of the aqueous phase was 11. A solution of 1 N HCl was then added until the pH of the aqueous phase was 6-7. The aqueous phase was extracted with DCM (200 mL). The combined organic layers were dried (MgSO4) and concentrated. Chromatography of the residue gave the title compound as a white solid (2.5 g).

Source