Water → 5-Amino-2-(piperidin-1-yl)benzonitrile

HRID 2216388ノート

反応式

HRID 2216388 の反応式
[Cl-].[NH4+].O.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:11]([CH:14]=1)[C:12]#[N:13])([O-])=O>[Fe].C(O)C>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[C:11]([CH:14]=1)[C:12]#[N:13]

参加物

6

反応物 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 48111995-Nitro-2-(piperidin-1-yl)benzonitrile

生成物 1

HCID 108457515-Amino-2-(piperidin-1-yl)benzonitrile収率 95.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

2-Chloro-5-nitrobenzonitrile (20 g) and piperidine (9.34 g) were added to acetonitrile (100 ml) and the mixture was stirred at the refluxing temperature for 1 hr. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from methanol to give 5-nitro-2-piperidinobenzonitrile (17 g). Subsequently, ammonium chloride (1.6 g) and iron powder (8.4 g) were added to a mixed solvent of water (40 ml) and ethanol (120 ml) and the mixture was heated to 65° C. 5-Nitro-2-piperidinobenzonitrile (10 g) was added by portions over 20 min and the mixture was stirred at the refluxing temperature for 30 min. The reaction mixture was ice-cooled and the reaction solution was filtrated. The solvent was evaporated under reduced pressure. An aqueous sodium hydroxide solution was added and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (8.3 g). melting point: 148-149° C.

後処理

  1. temperaturecooled
  2. filtrationthe reaction solution was filtrated
  3. customThe solvent was evaporated under reduced pressure
  4. additionAn aqueous sodium hydroxide solution was added
  5. extractionthe mixture was extracted with toluene
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. additionDiisopropyl ether was added to the residue
  10. customcrystallization
  11. customthe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-69559cd759084851b146b9365b7faacd
出典データセット
uspto-grants-2006_09
特許番号
US07112594B2

反応ノート

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