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

HRID 428940Notes

Reaction equation

HRID 428940 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

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 gmu 0.54 inmol) 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%).

Workup

  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

Sources & evidence

ORD record
ord-68a489b6cfb546199f6670c1739a9155
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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