4-Cyclopropylaniline → 2,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidine

HRID 2364817Notes

Reaction equation

HRID 2364817 reaction equation
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.[CH:29]1([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:36]2[C:35]2[CH:37]=[CH:38][C:32]([CH:29]3[CH2:31][CH2:30]3)=[CH:33][CH:34]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 122539274-CyclopropylanilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 672363922,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 42B (3.14 g, 5.64 mmol) and 4-cyclopropylaniline (6.01 g, 45.2 mmol) were combined in DMF (20 mL). The mixture was stirred at 50° C. under nitrogen for 3 hours. The reaction mixture was partitioned between 1M HCl and ethyl acetate. The organic layer was washed with brine three times, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%) to give the title compound (2.12 g, 76%) as a mixture of stereoisomers as a sticky solid.

Workup

  1. customThe reaction mixture was partitioned between 1M HCl and ethyl acetate
  2. washThe organic layer was washed with brine three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%)

Sources & evidence

ORD record
ord-17bd51fc61fa474fa6a85f8af53a5b00
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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