Piperazine → 2-Nitro-5-piperazinylbenzaldehyde hydrochloride

HRID 1649196ノート

反応式

HRID 1649196 の反応式
C(O[CH:4]([O:15]CC)[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])C.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CN(C)C=O>[ClH:11].[N+:12]([C:6]1[CH:7]=[CH:8][C:9]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:10][C:5]=1[CH:4]=[O:15])([O-:14])=[O:13]

参加物

4

反応物 2

HCID 4837PiperazineHCID 132362995-Chloro-2-nitrobenzaldehyde diethyacetal

生成物 1

HCID 132363002-Nitro-5-piperazinylbenzaldehyde hydrochloride収率 64.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2-Nitro-5-chlorobenzaldehyde diethyl acetal (138 g) was dissolved in 750 ml of dimethylformamide (DMF) and to the solution was added 250 g of anhydrous piperazine and stirred at 80° C. for 4 hours. After removing excessive piperazine and DMF by evaporation under reduced pressure, and a dilute aqueous sodium hydroxide solution was added to the residue to dissolve. Then, the solution was extracted with methylene chloride. The methylene chloride layer was washed with water and dried over sodium sulfate followed by removal of the solvent by distillation. To the residue was added 850 ml of isopropyl alcohol to dissolve, and to the solution was added 65 ml of concentrated hydrochoric acid and heated under reflux for 1 hour. After cooling, the crystals which precipitated were collected by filtration to give 93 g of 2-nitro-5-piperazinylbenzaldehyde hydrochloride, m.p. 195°-201° C.

後処理

  1. customAfter removing excessive piperazine and DMF
  2. customby evaporation under reduced pressure
  3. additiona dilute aqueous sodium hydroxide solution was added to the residue
  4. dissolutionto dissolve
  5. extractionThen, the solution was extracted with methylene chloride
  6. washThe methylene chloride layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. customfollowed by removal of the solvent by distillation
  9. additionTo the residue was added 850 ml of isopropyl alcohol
  10. dissolutionto dissolve
  11. additionto the solution was added 65 ml of concentrated hydrochoric acid
  12. temperatureheated
  13. temperatureunder reflux for 1 hour
  14. temperatureAfter cooling
  15. customthe crystals which precipitated
  16. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-fd58aa7a7f544857a9a592ea9ba71a67
出典データセット
uspto-grants-1983_11
特許番号
US04415572

反応ノート

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