Potassium Carbonate → 4-(4-benzylpiperazin-1-yl)benzaldehyde

HRID 2256874Notes

Reaction equation

HRID 2256874 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 759941-Benzylpiperazine

Product 1

HCID 27355074-(4-benzylpiperazin-1-yl)benzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of 4-benzylpiperazine (5.0 mL, 28.8 mmol), 4-flurobenzaldehyde (3.1 mL, 28.8 mmol)) and anhydrous K2CO3 (5.96 g, 43.1 mmol)) in DMF (50 mL) to -150° C. overnight. Cool the mixture to room temperature, partition between water and ether (Et2O), and extract with Et2O. Combine the Et2O extracts, wash with water and brine, dry over anhydrous Na2SO4 and concentrate in vacuo to obtain 7.91 g (98%) of 4-(4-benzylpiperazin-1-yl)benzaldehyde as a yellow solid of sufficient purity to be employed in Example 1 without further purification.

Workup

  1. temperatureHeat
  2. custompartition between water and ether (Et2O)
  3. extractionextract with Et2O
  4. washwash with water and brine
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9c771e2a0d4e45b4b484c9c15c0cc337
Source dataset
uspto-grants-1997_08
Patent number
US05656624

Reaction notes

Loading…