Piperazine → Methyl 2-(piperazin-1-yl)benzoate

HRID 278905Notes

Reaction equation

HRID 278905 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>O1OCCCC1>[C:4]([C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 11894Methyl 2-bromobenzoate

Product 1

HCID 10932975Methyl 2-(piperazin-1-yl)benzoateYield 26%

Reagents, catalysts & solvents 1

HCID 1385701,2-DioxaneSolvent

Procedure

To a solution of methyl 2-bromobenzoate (1.63 g, 17.8 mmol) in 1,6-dioxane (100 ml) at room temperature was added piperazine (15.3 g, 178 mmol) and K2CO3 (4.92 g, 35 mmol). The resulting mixture was heated to reflux for 7 days after which the reaction mixture was cooled to room temperature. The solvent and the excess piperazine were removed in vacuo along with heating with a hot water bath. The residue was dissolved in 1N NaOH solution, extracted with CH2Cl2 (6×30 ml), and dried over Na2SO4. The solvent was removed in vacuo to obtain 1-(2-carbomethoxyphenyl)-piperazine as a yellow oil (1.0 g, 26%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 7 days after which the reaction mixture
  3. customThe solvent and the excess piperazine were removed in vacuo along
  4. temperaturewith heating with a hot water bath
  5. dissolutionThe residue was dissolved in 1N NaOH solution
  6. extractionextracted with CH2Cl2 (6×30 ml)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-186d751b1f1b40cdaae2db0966c5af2d
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Reaction notes

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