n,n-Dimethyl{2-[4-benzyl-piperazinyl]phenyl}carboxamide → N,N-Dimethyl-2-(1-piperazinyl)benzamide

HRID 228110Notes

Reaction equation

HRID 228110 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14](CC2C=CC=CC=2)[CH2:13][CH2:12]1)=[O:4]>[Pd].CO>[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:4]

Participants

4

Reactant 1

HCID 21935201n,n-Dimethyl{2-[4-benzyl-piperazinyl]phenyl}carboxamide

Product 1

HCID 28749556N,N-Dimethyl-2-(1-piperazinyl)benzamideYield 84.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round-bottomed flask equipped with stirring was added N,N-dimethyl(2-[4-benzylpiperazinyl]phenyl)carboxamide (Step 2)(420 mg, 1.3 mmol), MeOH (10 mL), 10% Pd/C (Aldrich) (138 mg), and HCO2NH4 (409 mg, 6.5 mmol), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was filtered through Celite®, concentrated in vacuo, and redissolved in CH2Cl2 (20 mL). The reaction mixture was washed with a Na2CO3 (10%, 2×), H2O, brine, dried-over Na2SO4, filtered and concentrated in vacuo yielding N,N-dimethyl(2-piperazinylphenyl)carboxamide (255 mg). MS (ESI, pos. ion) m/z: 234 (M+H). Calc'd for C13H19N3O: 233.31.

Workup

  1. customTo a round-bottomed flask equipped
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2 h
  4. filtrationThe reaction mixture was filtered through Celite®
  5. concentrationconcentrated in vacuo
  6. dissolutionredissolved in CH2Cl2 (20 mL)
  7. washThe reaction mixture was washed with a Na2CO3 (10%, 2×), H2O, brine, dried-over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7854b3cc273146678812687c84a990b7
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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