Sodium Carbonate → Piperazin-1-yl-acetic acid

HRID 1989857Notes

Reaction equation

HRID 1989857 reaction equation
Br[CH:2](C1C=CC=CC=1)[C:3]([O:5]C)=[O:4].[N:13]1(C2C=CC(C#N)=CC=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[N:13]1([CH2:2][C:3]([OH:5])=[O:4])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 27339954-(Piperazin-1-yl)benzonitrile

Product 1

HCID 650402Piperazin-1-yl-acetic acidYield 183.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-bromo-2-phenylacetate (0.1 mol) was added dropwise to a mixture of 4-(1-piperazinyl)benzonitrile (0.1 mol) and Na2CO3 (90.15 mol) in DMF (250 ml), stirred at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated. The residue was dissolved in DCM, washed, dried, filtered and the solvent evaporated. The residue was triturated under DIPE, filtered off and dried, yielding 26.5 g of 1-piperazineacetic acid, 4-(4-cyanophenyl)-α-phenyl-, methyl ester (intermediate 5).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was triturated under DIPE
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-73802eaff36543358303b3369bad7838
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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