Potassium Carbonate → Benzaldehyde, 2-(3-(4-phenyl-1-piperazinyl)propoxy)-

HRID 1789368

Reaction equation

HRID 1789368 reaction equation
[Na].[OH:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].Cl.Cl.Cl[CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]1([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][O:2][C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[CH:5]=[O:6])[CH2:22][CH2:21]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123996821-(3-Chloropropyl)-4-phenylpiperazine dihydrochlorideHCID 86741752Sodium 2-formylbenzenolate

Product 1

HCID 55232Benzaldehyde, 2-(3-(4-phenyl-1-piperazinyl)propoxy)-Yield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.88 g of 2-hydroxybenzaldehyde sodium salt, 7.00 g of 1-(3-chloropropyl)-4-phenylpiperazine dihydrochloride, 6.80 g of potassium carbonate and 50 ml of dimethylformamide is stirred at 60° to 70° C. for 15 hours under nitrogen atmosphere, and is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ether. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=99:1). 5.42 g of 2-[3-(4-phenylpiperazin-1-yl)propyloxy]benzaldehyde are obtained as an oil.

Workup

  1. concentrationis concentrated under reduced pressure
  2. customto remove solvent
  3. additionWater is added to the residue
  4. extractionthe aqueous mixture is extracted with ether
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-84c56ccc3d8f4af7b42a8396c4f681d0
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Linked notes

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