Hydrochloric Acid → 3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane

HRID 1814033Notes

Reaction equation

HRID 1814033 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][C:16]=1F.[CH:21]12[CH2:26][CH:25]1[CH2:24][NH:23][CH2:22]2.Cl>CN(C=O)C.C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][C:16]=1[N:23]1[CH2:24][CH:25]2[CH:21]([CH2:26]2)[CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 131505233-Azabicyclo(3.1.0)hexane

Product 1

HCID 111954013-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Diisopropylethylamine (0.56 mL, 3.2 mmol) and 3,4-difluoronitrobenzene (0.184 g, 1.16 mmol) were added to a solution 3-aza-bicyclo[3.1.0]hexane (0.152 g of HCl salt, 1.28 mmol; prepared as described in U.S. Pat. No. 4,183,857) in DMF (3.2 mL). The mixture was heated for three days at 45° C. and then cooled to room temperature. The solution was diluted with ethyl acetate and washed with 0.5 M HCl, saturated NaHCO3, brine, and dried (MgSO4). The mixture was filtered and concentrated to give 3-(2-fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane as a yellow solid.

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. washwashed with 0.5 M HCl, saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c8accd7ee2a45738cf6d1e438992710
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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