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

HRID 1789370ノート

反応式

HRID 1789370 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5ac80b0aa0e5432ea6f8cf1cb67bf4af
出典データセット
uspto-grants-1987_08
特許番号
US04689327

反応ノート

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