Reaction #68869

Reaction equation

di-tert-butyl azodicarboxylate

4-(4-hydroxy-benzyl)-piperazine-1-carboxylic acid phenylamide

cyclohexanol

Ph3P

→

title compound

Yield 28.0%

4-(4-cyclohexyloxy-benzyl)-piperazine-1-carboxylic acid phenylamide

Yield 28.0%

Solvents

DCM

Conditions

Workup

1. 1
   Filtrationfiltered

Procedure

To a mixture of 4-(4-hydroxy-benzyl)-piperazine-1-carboxylic acid phenylamide (311 mg) and cyclohexanol (150 mg) in DCM (4 mL) was added polymer-supported Ph3P (500 mg) followed by di-tert-butyl azodicarboxylate (345 mg). The reaction mixture was shaken overnight, and filtered. Chromatography of the filtrate gave the title compound as a white solid (110 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.19 (m, 6H), 7.05-7.00 (m, 1H), 6.88-6.84 (m, 2H), 6.30 (s, 1H), 4.25-4.20 (m, 1H), 3.50-3.47 (m, 6H), 2.48-2.46 (m, 4H), 2.01-1.97 (m, 2H), 1.82-1.80 (m, 2H), 1.60-1.29 (m, 6H).

Source