Methyl Methacrylate → 3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid methyl ester

HRID 511108Notes

Reaction equation

HRID 511108 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O-]CC.[Na+].[CH3:18][O:19][C:20](=[O:24])[C:21]([CH3:23])=[CH2:22]>C(O)C>[CH3:18][O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH2:22][N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 974781-(4-Chlorophenyl)piperazineHCID 2723922Sodium ethoxide

Product 1

HCID 435387603-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Chloro-phenyl)-piperazine (392 mg; 2.0 mmol) and sodium ethoxide (150 mg; 2.21 mmol) are dissolved in ethanol (2 mL) and irradiated for 5 minutes in a mono-mode microwave oven at 60° C. 2-Methyl-acrylic acid methyl ester (400 μL; 4.0 mmol) is then added and the resulting mixture is irradiated for 50 minutes in a mono-mode microwave oven at 100° C. The reaction is concentrated under reduced pressure, diluted in ethylacetate (10 mL) and extracted with water (2×5 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure to afford the desired product (586 mg; 1.98 mmol).

Workup

  1. customirradiated for 5 minutes in a mono-mode microwave oven at 60° C
  2. customthe resulting mixture is irradiated for 50 minutes in a mono-mode microwave oven at 100° C
  3. concentrationThe reaction is concentrated under reduced pressure
  4. additiondiluted in ethylacetate (10 mL)
  5. extractionextracted with water (2×5 mL)
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1929e542cf34705921f94f2e4f0f100
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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