1-Phenylpiperazine → 2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]benzaldehyde

HRID 1789370Notes

Reaction equation

HRID 1789370 reaction equation
C1[O:15][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:11][CH2:12][CH2:13]Cl)OC1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:13][CH2:12][O:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[CH:4]=[O:15])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 138143232-(2-Chloroethyloxy)benzaldehyde ethyleneacetal

Product 1

HCID 138089772-[2-(4-Phenylpiperazin-1-yl)ethyloxy]benzaldehydeYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2.29 g of 2-(2-chloroethyloxy)benzaldehyde ethyleneacetal, 1.73 g of N-phenylpiperazine, 1.50 g of anhyrous potassium carbonate and 15 ml of dimethylformamide is stirred at 70°-80° C. for about 18 hours under argon atmosphere. The reaction mixture is concentrated under reduced pressure to remove dimethylformamide. 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 dissolved in 10 ml of methanol, and 10% hydrochloric acid is added thereto. The mixture is heated at 60° to 70° C. for 10 to 20 minutes, and then is made alkaline with 10% sodium hydroxide solution and 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, ethyl acetate:chloroform=2:8). 1.33 g of 2-[2-(4-phenylpiperazin-1-yl)ethyloxy]benzaldehyde are obtained as a colorless oil.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove dimethylformamide
  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. dissolutionThe residue is dissolved in 10 ml of methanol
  10. addition10% hydrochloric acid is added
  11. temperatureThe mixture is heated at 60° to 70° C. for 10 to 20 minutes
  12. extractionextracted with ether
  13. washThe extract is washed with water
  14. customdried
  15. concentrationconcentrated under reduced pressure
  16. customto remove solvent
  17. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=2:8)

Sources & evidence

ORD record
ord-5ac80b0aa0e5432ea6f8cf1cb67bf4af
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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