7-Azabicyclo(2.2.1)heptane → 7-(3-Bromo-4-nitrophenyl)-7-azabicyclo[2.2.1]heptane

HRID 383399

Reaction equation

HRID 383399 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]12[NH:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N:18]2[CH:12]3[CH2:17][CH2:16][CH:15]2[CH2:14][CH2:13]3)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 1360937-Azabicyclo(2.2.1)heptaneHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

Product 1

HCID 575168467-(3-Bromo-4-nitrophenyl)-7-azabicyclo[2.2.1]heptaneYield 255.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-4-fluoro-1-nitro-benzene (250 mg, 1.14 mmol) in DMSO (2 mL) was added 7-azabicyclo[2.2.1]heptane (182 mg, 1.36 mmol) portion-wise. The reaction was stirred at 80° C. for 24 h. The reaction was quenched with water and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with 1 N HCl, dried over MgSO4, filtered and concentrated in vacuo to provide 7-(3-bromo-4-nitrophenyl)-7-azabicyclo[2.2.1]heptane (864 mg, 98% yield). LC/MS m/z 298.5 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic extracts were washed with 1 N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df39a32b2f1d487dbab50ed4db68f71e
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Linked notes

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