Methyl Benzoate → 1-Benzoylpiperazine

HRID 992355Notes

Reaction equation

HRID 992355 reaction equation
C[CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[Al](Cl)(C)C.[Al](Cl)(CC)CC.[C:18](OC)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl>[C:18]([N:3]1[CH2:2][CH2:7][NH:6][CH2:5][CH2:4]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 7150Methyl BenzoateHCID 7277Diethylaluminum chlorideHCID 14798Sodium HydroxideHCID 660572-MethylpiperazineHCID 79147Chlorodimethylaluminum

Product 1

HCID 7626541-BenzoylpiperazineYield 105,129.398%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methylpiperazine (10.0 g, 0.1 mol) in dry CH2Cl2 (500 ml) under argon was added a solution of 1.0 M Me2AlCl or Et2AlCl in hexanes (100 ml, 0.1 mmol) and methyl benzoate (12.4 ml, 0.1 mmol) at room temperature. The reaction mixture was then stirred for 2 days before 2N NaOH (200 ml) was added. Aqueous layer was extracted with EtOAc (3×100 ml). The combined organic layer was dried over MgSO4 and concentration of solution provided 20.0 g of crude product (98%), with was pure enough for the further reactions.

Workup

  1. additionwas added
  2. extractionAqueous layer was extracted with EtOAc (3×100 ml)
  3. dry with materialThe combined organic layer was dried over MgSO4 and concentration of solution

Sources & evidence

ORD record
ord-08635df05a534bdeb0dfde8159a0fd53
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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