Ethanol → 3-(3-Hexyl-6-isopropyl-3-azabicyclo[3.1.0]hex-6-yl)aniline

HRID 1826451노트

반응식

HRID 1826451 반응식
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH:22]([CH3:24])[CH3:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)C.[Cl-].[Ca+2].[Cl-]>O.[Fe]>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[NH2:19])[CH:22]([CH3:24])[CH3:23])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

6

반응물 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 221411753-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane

생성물 1

HCID 221413693-(3-Hexyl-6-isopropyl-3-azabicyclo[3.1.0]hex-6-yl)aniline수율 104.8%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

To a stirred suspension of 3-hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane (Preparation 60, 0.18 g, 0.54 mmol), ethanol (15 ml) and iron powder (0.27 g, 4.88 mmol) was added calcium chloride (0.06 gm 0.54 mmol) in water (3 ml). The reaction mixture was heated under reflux for 3 h and then filtered through a pad of Celite®, the mother liquors were concentrated in vacuo. The residue was dissolved in dichloromethane and filtered again through a Sep-Pak® Plus cartridge containing silica (1.5 g), (Water Division Millipore), to remove any residual iron salts and then concentrated to give the crude title compound as a yellow solid (0.17 g, 100%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationfiltered through a pad of Celite®
  4. concentrationthe mother liquors were concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. filtrationfiltered again through a Sep-Pak® Plus cartridge
  7. additioncontaining silica (1.5 g), (Water Division Millipore),
  8. customto remove any residual iron salts
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3ef871c7b0b9423d8691b73add77e472
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049444B2

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