1-Benzyl-4-(4-nitrophenyl)piperazine → 4-(4-Benzylpiperazin-1-yl)aniline

HRID 479379

反応式

HRID 479379 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-]>O.C(O)C.C(O)(=O)C.[Zn]>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineHCID 5284359Calcium Chloride

生成物 1

HCID 7372594-(4-Benzylpiperazin-1-yl)aniline収率 96.7%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 86584229Acetic acid ethanol water溶媒

実験手順

4-(4-Benzyl-1-piperazinyl)-1-nitrobenzene (2.6 g; 8.9 mmol) synthesized by the above process and zinc powder (3.2 g; 48 mmol) were added to a solution of calcium chloride (665 mg; 6.0 mmol) in water-ethanol-acetic acid (12 ml-55 ml-1.2 ml), and the mixture was stirred under reflux for 15 minutes in a bath controlled at 110° C. Insoluble substances were removed from the reaction mixture by suction filtration through Celite, and the filtrate was concentrated under reduced pressure. A saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue to conduct extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus-obtained crude crystals were recrystallized from benzene-n-hexane to obtain 2.3 g (yield: 96%) of 4-(4-benzyl-1-piperazinyl)aniline as pale brown needles (melting point: 137-138° C.).

後処理

  1. temperatureunder reflux for 15 minutes in a bath
  2. customcontrolled at 110° C
  3. customInsoluble substances were removed from the reaction mixture by suction filtration through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue
  6. extractionextraction with chloroform
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe thus-obtained crude crystals
  10. customwere recrystallized from benzene-n-hexane

出典と根拠

ORDレコード
ord-eb341ba792304dabbe20cdd9ec0a2ed7
出典データセット
uspto-grants-2003_11
特許番号
US06645957B2

関連ノート

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