Reaction #78116

Reaction equation

N1-[1-(4-pyridyl)piperidin-4-ylmethyl]-1,2-benzenediamine

pyridine

4-methoxybenzoyl chloride

→

title compound

Yield 17.0%

N1-(4-methoxybenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-1,2-benzendiamine

Yield 17.0%

Solvents

chloroform

chloroform

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc
3. 3
   WashThe organic layer was washed with 1 N NaOH (2×), water (3×), brine (1×)
4. 4
   Dryingdried (K2CO3)
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by RPHPLC

Procedure

A solution of N1-[1-(4-pyridyl)piperidin-4-ylmethyl]-1,2-benzenediamine (212 mg, 0.75 mmol) and pyridine (4 mL) in chloroform (2 mL) at 0° C. was treated with a solution of 4-methoxybenzoyl chloride (128 mg, 0.75 mmol) in chloroform. The mixture was allowed to warm to room temperature and stir for 17 h. The mixture was concentrated and the residue was dissolved in EtOAc. The organic layer was washed with 1 N NaOH (2×), water (3×), brine (1×), dried (K2CO3), and concentrated. The residue was purified by RPHPLC, yielding 52 mg (17%) of the title compound as a hydrochloride salt.

Source